Bootstrap vs Venture Capital with Rob and Chris Taylor

Rob is a serial software entrepreneur having built, scaled and exited multiple B2B and B2C venture-backed technology businesses. Most recently, Rob was co-founder and CEO of Convey, a pioneer in logistics and supply chain visibility software for some of the largest global retailers such as The Home Depot, Costco, Walmart and QVC. Convey was acquired by project44 in 2021 for $255M. Prior to Convey, Rob was President of BlackLocus, another retail SaaS software business that was acquired by The Home Depot for $55M within eighteen months of taking on the first venture capital investment. Rob then spent two years building Home Depot's Innovation Lab in Austin, TX. Prior to BlackLocus, Rob served as EVP & GM of TrueCar, an online technology business reinventing how cars are purchased & sold on the internet. TrueCar completed its IPO in 2014 after raising several hundred million dollars over the preceding four years.   

Chris is a dad, husband, serial entrepreneur, CEO advisor, and bootstrap evangelist.  Chris founded Square Root in 2006 after a 10 year career at Trilogy Software.  He bootstrapped Square Root for 15 years until he sold it to an automotive strategic, CDK Global in 2021. Now Chris helps other entrepreneurs overcome their challenges and celebrate their wins.

Square Root’s SaaS platform, CoEFFICIENT, helped the world’s leading automotive brands use data science to drive dealership performance.  Culture is a huge focus for Chris, and Square Root received many culture accolades including being named the 2nd best US workplace by FORTUNE, a top innovator by Fast Company, and one of PEOPLE magazine’s top companies that care.

Chris graduated Phi Beta Kappa from Carnegie Mellon with degrees in Computer Science, Mathematics, and Cognitive Psychology. 

Outside of entrepreneurship, Chris enjoys adventuring with his wife and two daughters, cycling, and a nice glass of wine.