Ryan Caldbeck and his co-founder Rory Eakin founded what has become one of the most innovative investment platforms I’ve ever seen with their award-winning company, CircleUp. In short, they use machine learning analysis to find and fund amazing companies in the consumer packaged goods space, companies like Halo Top, Rebbl, Smarty Pants vitamins — and we actually share some of those companies like Halo Top. But, being the founder of an innovative investment approach that is hitting its stride is only the above-the-line version of Ryan's story.

Last year, Ryan started sharing what his entrepreneurial experiences have really been like. His open and candid writing on twitter is shared within founder circles more than any other writing, because in a world of posturing and BS, he has begun to turn the tide on with something as simple as honesty— something the entrepreneurial world is craving.

We talk about what he’s shared, what he thinks a lot about, where we can do better, what it’s really like to go through a “Pivot” with a capital P. He does it all with a contagious sense ownership and accountability, which is why I think he is a major force in evolving the conversation of what it’s like to be a founder.

Email James questions at [email protected] Follow us on Twitter (twitter.com/gobelowtheline). "Below the Line with James Beshara" is brought to you by Straight Up Podcasts LLC