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 (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.lennyspodcast.com/relentless-curiosity-radical-accountability-and-hubspots-winning-growth-formula-christopher-mil/• FlashTags: A Simple Hack for Conveying Context Without Confusion: https://www.onstartups.com/flashtags-a-simple-hack-for-conveying-context-without-confusion• What it means to “disagree and commit”: https://news.ycombinator.com/item?id=16949021• A Simple Decision Framework: Debate, Decide and Unite: https://connectingdots.com/p/debate-decide-unite• Dharmesh Shah’s Frameworks for Creating a $1 Billion Net Worth: https://hakune.co/dharmesh-shah-networth/• Zip: https://ziphq.com/• The HubSpot Culture Code: Creating a Company We Love: https://blog.hubspot.com/blog/tabid/6307/bid/34234/the-hubspot-culture-code-creating-a-company-we-love.aspx• How defining values and culture helped Airbnb achieve worldwide success: https://lattice.com/library/how-defining-values-and-culture-helped-airbnb-achie• What is SQL?: https://aws.amazon.com/what-is/sql/• GrowthBot: https://community.hubspot.com/t5/Releases-and-Updates/Meet-GrowthBot-from-HubSpot-Labs/ba-p/417985—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe