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Chris Cunningham

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


Chris has launched three early-stage venture funds to help scale the C2V brand and has invested in over 45 portfolio companies.


Chris was the CEO and Co-founder of appssavvy, a pioneer in mobile native advertising, ultimately driving $70 million in revenues to the app ecosystem.


He is a LP in Bowery Capital and Tech Stars and has held executive roles at Unacast and Ironsource, a now $11B mobile technology company.

He has been named one of the "Most Important People in Mobile Advertising" by Business Insider and 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 would 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
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