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On October 13th 2020 I stepped down as CEO of CircleUp, the company I started in 2011 with my co-founder, Rory Eakin. Leaving the best job I ever had — at the company I helped to create — was difficult and confusing. …


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Navigating the private markets today is the equivalent of hailing a cab during rush hour or finding a newly released movie at a nearby Blockbuster ten years ago. Before technology intervened, you had to be in the right place at the right time. Decision-making in the private markets is just as circumstantial: it is opaque, reliant on personal networks, and largely driven by heuristics.

Closing a deal is a resource-intensive, relationship-based process for private companies. …


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All,

I want to follow up on my email this weekend about the murders of Ahmaud Arbery, Breonna Taylor, George Floyd and Tony McDade. These atrocities are only some of the more recent acts of race-related hate and violence. There have been more than any of us can know. The sadness, pain, and fear that our communities are expressing now is the culmination of both explicit and implicit prejudice that millions of people experience every single day.

Over the past few days, my own frustration, anger and disappointment have only grown. How can we fix this deeply broken system that claims to provide liberty, equality, and justice for all? I felt unsure of how to help as this all started to unfold 3 days ago. Since then, my confusion has lessened. …

Ryan Caldbeck

Founder and Executive Chairman @CircleUp. Follow me on Twitter @ryan_caldbeck

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