This podcast episode examines vertical market software (VMS) and vertical SaaS, discussing the challenges VMS companies faced due to COVID-19 and how vertical SaaS enabled businesses to adapt, such as Toast helping small businesses survive by enabling online delivery. It also explores the characteristics and challenges of investing in vertical SaaS businesses, delving into concepts such as gross retention and multi-product strategies. Additionally, it examines strategies for effectively serving merchants through a multi-product approach and the creative strategies employed by entrepreneurs to build successful businesses. Finally, it discusses the opportunities and challenges in the VMS market, emphasizing the importance of careful market evaluation and a nuanced investment approach.