Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO)

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—Brought to you by:• Explo—Embed customer-facing analytics in your product• Vanta—Automate compliance. Simplify security• LinkedIn Ads—Reach professionals and drive results for your business—Find the full transcript at: https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building—Where to find Dharmesh Shah:• X: https://twitter.com/dharmesh• LinkedIn: https://www.linkedin.com/in/dharmesh/• Website: https://dharmesh.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Dharmesh’s background(04:20) Fun facts about Dharmesh(06:31) His data-oriented approach to public speaking(11:45) Advice for adding humor to your presentations(15:28) Why he has no direct reports(18:46) You can shape the universe to your liking(20:02) Lessons from building HubSpot(23:43) Contrarian ways of running a company(37:26) Fighting the second law of thermodynamics (