Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO‪)‬ Lenny's Podcast: Product | Growth | Career

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
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Find the full transcript at: https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building
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Where to find Dharmesh Shah:
• X: https://twitter.com/dharmesh
• LinkedIn: https://www.linkedin.com/in/dharmesh/
• Website: https://dharmesh.com/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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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
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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