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Dirty, Dangerous, and a Little Dull: Chris Cunningham of C2V

Kevin welcomes Chris Cunningham, a true living legend in the digital space and a 20-year media and tech veteran who is a serial entrepreneur turned early-stage venture capitalist. Chris recently launched a $10 million early-stage venture to fund the C2V brand. He talks about how they select the brands in their portfolios. The guys give their real thoughts for better or worse on the Bay Area, comparing Shrek to Silicon Valley, and a few examples of the old economy legacy industries that are ripe for disruption. It’s a down-and-dirty discussion about disrupting the industries that may or may not be ready.


[4:02] Chris discusses C2V and how they invest in verticals that have had stagnant productivity but are products and services we touch and utilize every day of our lives.

[6:57] What do Silicon Valley and Shrek have in common?

[7:24] San Francisco is oversaturated and overpriced, and deals are overvalued.

[10:00] It’s not just about the talent, but looking at the problems that are being solved and how they are going about solving those issues.

[14:08] Is it really mature to be investing in Web3 and NFTs?

[15:40] Chris talks about the process of finding companies to run.

[18:40] How has remote work and going virtual shifted things?

[19:31] Chris discusses deal flow and more on how they select the companies.

[24:01] Your deck is your best friend, and will then be the next step to possibly get you a 30-minute Zoom or phone call.


  • [5:56] “It’s dirty, dull, and dangerous because these verticals are extremely boring, very sleepy, not that sexy. And that’s why we like them.” — Chris
  • [7:24] “Listen. We don’t hate on the Bay Area or San Francisco, but here’s the truth. It’s oversaturated. It’s overpriced. Deals are overvalued. Founder expectations are absurd.” — Chris
  • [24:10] “It’s not a shark tank model. It couldn’t be the furthest thing.” — Chris
  • [24:14] “The deck unlocks a 30-minute zoom.” — Chris

Mentioned in This Episode:

Chris Cunningham — C2 Ventures