What was Ryan's first academic love in high school? What opportunity did Ryan uncover by responding to a Craigslist advertisement? Why did Ryan decide to return to his original path after an enjoyable stint in consulting? What attribute of MIT culture appealed to Ryan and convinced him to apply to Sloan for an MBA? What part-time job did Ryan land at MIT that gave him special insight into the campus's eccentricities? How did Ryan end up founding a screen writing software business? How did Ryan pivot this failed idea into a lucrative marketplace business? What hard lesson about unit economics did Ryan learn during this period? How did Ryan connect the dots between data, B2B, and climate policy to start a new tech business? What did Ryan admire about Stripe that he applied to the permit data space with Shovels? Why is collecting and aggregating local building permit data so challenging? What insights has Shovels uncovered around permit activity and different types of climate disasters? What is the permit cloud that Shovel's is uncovering that indicates early signal about a larger infrastructure project? How is Shovels providing insight into available trade resources for intensive projects such as data centers?

Ryan Buckley - CEO and co-founder of Shovels, joins Proptech Espresso to answer these questions and discuss how his early childhood interest in roller hockey exposed him to the parking lots of seminal internet titans like Netscape and Silicon Graphics.