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 (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 decision-making 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 — Referenced: • WordPlay: https://wordplay.com/article/unlimited • ChatSpot: https://chatspot.ai/ • Indian-origin entrepreneur buys ‘chat.com’ for over $10 million, then sells, donates $250,000 to Khan Academy: https://www.businesstoday.in/technology/news/story/indian-origin-entrepreneur-buys-chatcom-for-over-10-million-then-sells-donates-250000-to-khan-academy-382907-2023-05-26 • Kipp Bodnar on LinkedIn: https://www.linkedin.com/in/kippbodnar/ • The surprising metric presenters should analyze: https://lars-sudmann.com/the-surprising-metric-presenters-should-analyze/ • SoloWare: https://www.linkedin.com/posts/dharmesh_for-3-decades-now-in-addition-to-my-day-activity-7166500611247583232-kZgb/ • Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan/ • First Principles: Elon Musk on the Power of Thinking for Yourself: https://jamesclear.com/first-principles • Peter Thiel on LinkedIn: https://www.linkedin.com/in/peterthiel/ • The second law of thermodynamics: https://en.wikipedia.org/wiki/Second_law_of_thermodynamics • What is an SMB?: https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business • Shopify: https://www.shopify.com/ • Relentless curiosity, radical accountability, and HubSpot’s winning growth formula | Christopher Miller (VP of Product, Growth and AI): https://www.l