About Us:

C2 Ventures is an early stage investment platform.  We bridge the gap between founders and capital through content, connections and experience.  In addition to making direct, venture investments, C2V supports its companies through capital raises, exits, commercial scaling, financial and operational support and advice, and promotional content.

To-date, C2V has provided advice and support for more than 20 companies, raised more than $20 million in seed and later-stage funding, and has supported 3 of its 4 portfolio company exits.
We believe the 75% failure rate of startups in their first two years is a statistic, not an inevitability.

Core Beliefs

  • Most failures are due to basic execution mistakes
  • These mistakes are avoidable
  • Experienced advisor engagement is an effective mitigant

Keys to Our Approach

Hands On Advice

  • Driving revenue growth and market traction
  • Execution, growth and cash management modeling
  • Avoiding common early-stage management mistakes
  • Identifying & executing on pivot/exit opportunities

Content Engine

  • Broad portfolio company exposure
  • Accelerated brand awareness and product adoption  
  • Increased C2V appeal & differentiation for top founders


“I love how accessible C2V is - text or phone and when we talk, I get your undivided attention. I also love that you’ve been there done that as a founder Bc you can relate to my situation in ways I don’t get with traditional VCs.”

“Chris has been the ideal early stage investor for Narrative and has helped tremendously as we've grown. His contributions have manifested themselves in a few key areas: Network: As others have pointed out. Chris knows everyone and just as important everyone like him. Anytime we've needed an introduction outside of our existing network Chris has delivered. Advisor: Being an entrepreneur himself Chris has always been there to talk through some of the challenges big or small in running a company. While this makes him "hands on" he isn't omnipresent. In that way he strikes the perfect balance of adding value without distracting from the day to day operations of the business.Friend: Above all else Chris is a genuinely good guy. Starting a company is hard enough without being surrounded by people you wouldn't hang out with IRL.”

“Chris is an investor in Uru, as well as an advisor. He has a seemingly omniscient view into everything happening in the advertising and digital media landscapes and, as a result, his advice is consistently spot-on. His energy is unflagging and he's a great guy to boot. We absolutely could not have gotten this far without Chris."

“Chris is an investor and an advisor to Arbor. He's very dedicated to helping us succeed and goes above and beyond to help with that cause. He's incredible at connecting people because he knows them all. We're extremely happy to have Chris helping out with Arbor."

"Chris is one of our investors/advisors and is an incredible value add. Where a lot of investors are happy to be involved at a high level, Chris gets deep to figure out what we need and help us execute. He's a really well-connected guy. If you have the opportunity to work with him, you should stop thinking and act."

"In the world of operationally driven investors, Chris is the best. He gets his hands dirty, rolls up his sleeves and does the work traditional VC's won't do"

"It’s simple. If you have an opportunity to partner with Chris, do it"

"In the world of advisors, Chris is the ultimate "players' coach". He looks out for the people in his circle and is constantly looking for ways to give you a leg up, whether it be a relatable ear, relevant intros, or guidance on key strategic decisions. He's been a huge asset to me as I've evolved as a founder and leader. Every time I interact with him I leave more confident and energized. Boss."

Our Team:

20+ years of startup and high-growth enterprise experience as Operator/CFO and Founder/CEO and 20+ years of asset management experience

Chris Cunningham

Chris Cunningham is a 20-year tech industry veteran and an active tech startup investor via C2 Ventures, which has invested in 17 companies and generated returns trending well ahead of industry averages for funds of the same vintage, with four exits to date. C2 Ventures is an operationally driven venture platform that takes an active role with founders. C2V invests in leading NY/SF venture firms and is also a Limited Partner in Bowery Capital and Tech Stars.

Chris was most recently President of Unacast, where he was the first employee in the U.S. to grow the business from zero revenue to $2MM in ARR within 18 months, which led to raising $20MM in total investment capital. Prior to that, he led U.S. operations as VP at IronSource, now a billion-dollar valuation company on the verge of an IPO.
Chris sold his prior company, appssavvy, the world’s first platform focused on monetizing Facebook apps through native advertising, to IronSource. He ran appssavvy for seven years as founder and CEO, and prior to that, he ran commercial efforts for Webs.com, which was acquired by VistaPrint for $117MM.
Over the span of his career, Chris has been responsible for generating more than $250M in net new ad revenue through 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 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

Following more than 10 years 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 a privately held trading firm as its CFO and tasked with leading a turnaround of the company, which had suffered serious growing pains due primarily to financial and strategic mismanagement. In addition to building most of the firm’s financial infrastructure from scratch, Matt was able to overhaul the cash flow and risk-management systems for the firm and one of its subsidiaries, while revamping and scaling its credit facilities and leading the process of divesting non‐performing and non‐core assets. These efforts led to the company’s most profitable two‐year period, restoring the balance sheet to a position of solvency and positioning it for accelerated growth.

Most recently, Matt has been running his own consulting business where he provides capital raising and outsourced CFO services for several privately held trading companies and startups.

Matt comes to C2V from a career in finance where he primarily focused on working with and for owner‐operated, high‐growth companies in a variety of industries. Matt will be tasked with building and overseeing the fund’s financial infrastructure and will be an integral part of C2V’s investment selection process, as well as our advisory‐focused approach to managing our early stage portfolio. We look forward to leveraging Matt’s experience and network within the institutional finance and fintech industries, as well as his experience in building and refining financial infrastructure, models, and strategic direction to give our founders the analytical tools to plan for and manage their companies’ growth, while optimizing their use of capital and other finite resources.

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