Ian Landsman, founder of HelpSpot, shares his journey of 20 years in bootstrapping a successful customer service software company. He discusses the transition from on-premises software to SaaS, highlighting the unique advantages of each model, especially in regulated industries. The conversation also touches on the financial challenges of B2B applications and the importance of community support. Lastly, Landsman explores the transformative impact of AI on customer service, addressing both opportunities and potential disruptions in the industry.