About Me

I’m a founder, operator and investor based in the Bay Area. I’m a dad of three and husband to Kim.

I co-founded the technology company CircleUp in 2011 and served as CEO before transitioning to a Chairman role in 2020. Before that, I was a growth investor.

I’m passionate about having an impact on the people, organizations and world around me. I care a lot about who I spend my time with and on what projects. I don’t believe in the airplane test. I choose to work with people who know their values and live by them – particularly those who demonstrate integrity, work ethic, horsepower, teamwork, and pride. I’m drawn to people who are open to new ideas and hungry to grow and learn. I gravitate toward those who are intellectually honest and thirst for data when making decisions. Trust is the most important component for me in any relationship. I define trust as: Trust = (Reliability x Credibility x Authenticity) / Self-Interest.

I believe in thinking in public. Putting out content forces me – and hopefully others – to embrace new perspectives that drive clarity of thought.

I believe Inputs matter – They are the process by which we achieve results. Improving the process of decision-making intrigues me. Identifying what we can control and what is left to chance inspires me.

I grew up in Vermont and moved to California in 2003 for graduate school at Stanford. I enjoy spending time with my family, reading and playing basketball (that bend in my nose is from an errant elbow.) I devour cheddar cheese, Vermont maple syrup and buffalo wings. I’m fascinated by the MCU and Star Wars (except Solo).

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About CircleUp

CircleUp is a fintech company founded in 2011 by Ryan Caldbeck and Rory Eakin. It started as a marketplace that connected investors and companies until the company pivoted in 2017. CircleUp harnesses the power of data to provide capital and resources to emerging consumer brands. With its proprietary technology platform, Helio, CircleUp is bringing the data-driven revolution that occurred in the public markets to the private markets – starting with consumer & retail. Helio algorithmically finds, classifies and evaluates private companies to power more objective and efficient decision-making. CircleUp has built several applications on top of this technology, including an equity investing business, a credit business and a SaaS business. On a mission to help entrepreneurs thrive, CircleUp has facilitated investments for 600 businesses to date.

CircleUp was honored as one of Fast Company’s Top 10 Most Innovative Companies in Data Science, LendIt’s Small Business Lending Platform of the Year, and FinTech Breakthrough’s Best Institutional Investment Platform, and was named to the CNBC Disruptor 50, CB Insights FinTech 250, Forbes FinTech 50 (Most Innovative Financial Technology Companies), KPMG 50 Best Fintech Innovators, and Entrepreneur’s Best Entrepreneurial Companies in America.

CircleUp is backed by world-class investors including Union Square Ventures, GV, Canaan Partners, QED Advisors, TPG, Temasek, Rose Park Advisors, and others. Learn more at http://www.circleup.com