Dharmesh Shah is the cofounder 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 topranking 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 dataoriented approach to public speaking
• How he developed HubSpot’s culture code
• The decisionmaking 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

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Find the full transcript at: https://www.lennysnewsletter.com/p/le...

Where to find Dharmesh Shah:
• X:   / dharmesh  
• LinkedIn:   / dharmesh  
• Website: https://dharmesh.com/

Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X:   / lennysan  
• LinkedIn:   / lennyrachitsky  

In this episode, we cover:
(00:00) Dharmesh’s background
(04:20) Fun facts about Dharmesh
(06:31) His dataoriented 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
(40:29) The importance of simplicity in running a business
(45:22) Succeeding in the SMB market
(50:29) Zigging when others are zagging
(54:17) When it makes sense to go “wide and deep”
(57:33) Using flashtags to communicate opinions
(01:02:44) HubSpot’s decisionmaking process
(01:09:41) Deciding what ideas to invest in
(01:15:26) Defining and maintaining company culture
(01:30:46) The potential of AI
(01:37:03) Practical advice for learning AI
(01:40:07) Where to find Dharmesh

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Lenny may be an investor in the companies discussed.