Venture Capital Cartoons

I seemed to have spent most of my career around Venture Capital. Early on, I had the chance to make investments in founders at a corporate VC fund, which ultimately became the reason I did my own startups … because I realized I knew so little.

With the experience of sitting on both sides of the table, as well as taking multiple companies from concept to exit, I think I have a decent understanding of the industry and mindset. So it was a wonderful opportunity to be picked up by Fortune Magazine’s Term Sheet, the industry’s leading daily newsletter with over 100K readers, to be their cartoonist.

The editors wanted a different experience, so I decided to lean into pop art and make the cartoons a standalone (i.e. no explanation), single panel experience, which has made it a rod for my own back! The industry is great fun to cover, with lots of inside jokes and tribal cultural behavior, interspersed with the occasional ego that needs a puncture.

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They’re invaluable for illustrating fundamental principles such as startup funding rounds, investor pitches, and entrepreneurial risk-taking in a visually engaging manner. Whether depicting the ups and downs of startup investments or the dynamics of venture capitalists negotiating deals, these cartoons provide a lighthearted yet informative perspective.