Chris Cunningham

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A 20-year media and tech entrepreneur turned early-stage venture capitalist.


As an angel investor, Chris invested in 18 tech start-ups; four have sold for cash, and others like Petal, Narrative, and Advisr continue to increase in value.


Chris launched a $10M early-stage venture fund to scale the C2V brand and invest in more companies.


Chris is an LP in Bowery Capital and Tech Stars. He also held executive roles at Unacast and Ironsource, a now $2B privately held mobile technology company that recently sold a $500MM cash stake to private equity.

Chris was the CEO and Co-founder of Appssavvy, a start-up he started from his Soho apartment back in 2006. Appssavvy was the industry's first platform that monetized Facebook apps and games through native advertising with fortune 500 brand advertisers. Appssavvy drove over $80MM in revenue to the app ecosystem on both Facebook and mobile devices.


Before Appssavvy, he was the SVP for, which was acquired by VistaPrint for $117MM and is now a $1.5B company.

Over the span of his career, Chris and his team have been responsible for generating more than $250M in net new ad revenue through innovative new products, and he has succeeded in raising more than $100 million in venture capital while recruiting and growing numerous companies.

Chris has been named one of the "Most Important People in Mobile Advertising" by Business Insider, as well as being named an Ernst & Young “Entrepreneur of the Year Finalist” two years in a row.

Chris graduated from the University of North Carolina Greensboro in 1997 with an Economics degree. He has two sons, runs marathons and triathlons, and he'd rather be scuba diving.

Matt Olivo

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With a 20-year career in finance, primarily focusing on working with owner‐operated, high‐growth companies in a variety of industries, Matt joined Chris as General Partner at C2 Ventures.

Following more than a decade in banking, Matt co‐ran a $1 billion trade finance portfolio, initially under the umbrella of a boutique hedge fund manager and later as part of The Carlyle Group.

Matt was subsequently hired by one of Carlyle’s portfolio companies as its CFO and tasked with building most of the firm’s financial infrastructure from scratch.

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He revamped and scaled its credit facilities and led the divesting of its non‐performing and non‐core assets, leading to its most profitable ever 2-year period.


As a General Partner of C2V and its COO & CFO, Matt has built and oversees the fund’s infrastructure and has been an integral part of our investment selection process, leveraging his two-plus decades of experience in evaluating owner-operators of privately held companies as well as applying the deep financial and operational analysis of prospective investments that, while the hallmark of traditional fund management, is exceedingly (and unfortunately) rare in the early-stage venture world. 

Matt shares his experience, network, and expertise with our portfolio companies, assisting with financial modeling, capital structure optimization, financial and operational infrastructure building, and growth and cash management strategies. Matt holds a BA from Colgate University and is a CFA charterholder. He is a member of the CFA Society and New York Society of Security Analysts and would generally instead be skiing or playing the guitar with his two kids.

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C2V is everything we hoped for in investors. They feel like an extension of our team as opposed to outside investors that just help fund the company. As an early stage startup, you face uncertainty trying to figure out which direction to take. C2V has always been there to give their perspective on the challenges we are working through and also challenge our thinking.
Nick McHenry - One Shop | Co-Founder & CEO