This podcast episode explores the journey of PlanGrid, a construction software company founded in 2011, and the lessons learned from its success and acquisition. The episode highlights the importance of considering multiple stakeholders in enterprise software, such as buyers and sales order form signers, and investing in continuous improvement. It also discusses the challenges of managing people, establishing clear core values, and maintaining authenticity in leadership. The episode touches on the significance of self-selection in hiring, validating product-market fit, and the role of personal relationships in business. Additionally, it explores the benefits and challenges of building a remote company and provides insights into the fundraising and board meeting processes. Overall, the episode emphasizes the importance of understanding all aspects of a business, fostering a healthy work environment, and making strategic decisions for long-term success.