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: lennysnewsletter.com/p/lessons-… — Where to find Dharmesh Shah: • X: twitter.com/dharmesh • LinkedIn: linkedin.com/in/dharmesh • Website: dharmesh.com — Where to find Lenny: • Newsletter: lennysnewsletter.com • X: twitter.com/lennysan • LinkedIn: — In this episode, we cover: — Referenced: • WordPlay: • ChatSpot: • Indian-origin entrepreneur buys ‘chat.com’ for over $10 million, then sells, donates $250,000 to Khan Academy: • Kipp Bodnar on LinkedIn: • The surprising metric presenters should analyze: • SoloWare: • Brian Halligan on LinkedIn: • First Principles: Elon Musk on the Power of Thinking for Yourself: • Peter Thiel on LinkedIn: • The second law of thermodynamics: • What is an SMB?: • Shopify: • Relentless curiosity, radical accountability, and HubSpot’s winning growth formula | Christopher Miller (VP of Product, Growth and AI): • FlashTags: A Simple Hack for Conveying Context Without Confusion: • What it means to “disagree and commit”: • A Simple Decision Framework: Debate, Decide and Unite: • Dharmesh Shah’s Frameworks for Creating a $1 Billion Net Worth: • Zip: • The HubSpot Culture Code: Creating a Company We Love: • How defining values and culture helped Airbnb achieve worldwide success: • What is SQL?: • GrowthBot: — Production and marketing by . For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed.