THE TEAM
20+ YRS EXPERIENCE IN ASSET MANAGEMENT
STARTUP & HIGH-GROWTH ENTERPRISE
FOUNDERS | CEOS
OPERATORS
Chris Cunningham
The industry often describes Chris as “the honest VC”, a voice that cuts through the glossy narratives that dominate venture capital.
He speaks plainly about what it really takes to build something lasting, because founders deserve transparency, not spin.
Chris is a builder first. He has spent over 20 years in tech as a founder, operator, and executive, leading sales, scaling operations, and learning everything the hard way.
He co-founded appssavvy in the early days of mobile and Facebook, pioneering native advertising and growing the company to $70M in revenue.
After that chapter, he shifted to angel investing, writing early checks into scrappy founders and real companies before teaming up with Matt Olivo to launch C2 Ventures.
They’ve now raised three funds to back AI-driven startups solving problems in the dirty, dull, and dangerous industries, the overlooked backbone of the real economy.
C2V’s thesis is simple: embed AI where it actually works, in the hands of real people doing real work. That’s what gets Chris excited. No shiny demos, just ROI, workflow impact, and founders who know what it means to grind.
He also hosts the Superpowers podcast, where he talks to founders about what drives them when things get messy. And he’s the face of C2V’s In the Trenches video series, where he tells the unvarnished truth about startup life.
Chris has been named one of Business Insider’s “Most Important People in Mobile Advertising” and was a two-time Ernst & Young “Entrepreneur of the Year” finalist. He’s also an LP in Bowery Capital and TechStars, backing the next generation of innovative builders.
Outside of work, he’s an ice hockey and lacrosse coach for two boys.
Matt Olivo
Prior to co-founding C2V’s institutional business, Matt spent 20 years in traditional finance, (fixed income and project finance, as well as some M&A and private equity), primarily working with owner‐operated, high‐growth companies in a variety of industries.
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, revamping and scaling its credit facilities, and leading efforts to divest of 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, and has served on several portfolio company boards, including Somatic, Steelhead, and Condoit.
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 rather be skiing with his two kids or playing the guitar (ideally for the ‘90s grunge cover band he swears he’s going to start one day).
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.