Dharmesh Shah is the co-founder and CTO of HubSpot (currently valued at $30 billion) and one of the most fascinating founders I’ve ever met. Dharmesh is the keeper of HubSpot’s Culture Code, built ChatSpot (an AI chatbot built on top of HubSpot CRM) and a game called WordPlay (which grew to 16 million users), and also founded and writes for OnStartups, a top-ranking startup blog and community with more than 1M members. He’s also invested in 100+ startups including OpenAI, AngelList, Coinbase, and Dropbox. In our conversation, we discuss • The biggest lessons he has learned from building HubSpot • The importance of leaning into your strengths • Dharmesh’s data-oriented approach to public speaking • How he developed HubSpot’s culture code • The decision-making process at HubSpot • His contrarian approach to building products • Why founders and product teams are all fighting the second law of thermodynamics • How “flash tags” can save your teams time • How to decide what ideas are worth investing in