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Dharmesh Shah is the co-founder and CTO of HubSpot (currently valued at $30 billion) and one of the most fascinating founders I\u2019ve ever met. Dharmesh is the keeper of HubSpot\u2019s 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\u2019s also invested in\xa0100+ startups including OpenAI, AngelList, Coinbase, and Dropbox. In our conversation, we discuss:

\u2022 The biggest lessons he has learned from building HubSpot

\u2022 The importance of leaning into your strengths

\u2022 Dharmesh\u2019s data-oriented approach to public speaking

\u2022 How he developed HubSpot\u2019s culture code

\u2022 The decision-making process at HubSpot

\u2022 His contrarian approach to building products

\u2022 Why founders and product teams are all fighting the second law of thermodynamics

\u2022 How \u201cflash tags\u201d can save your teams time

\u2022 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:

\u2022 X: https://twitter.com/dharmesh

\u2022 LinkedIn: https://www.linkedin.com/in/dharmesh/

\u2022 Website: https://dharmesh.com/

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Where to find Lenny:

\u2022 Newsletter: https://www.lennysnewsletter.com

\u2022 X: https://twitter.com/lennysan

\u2022 LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Dharmesh\u2019s 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 \u201cwide and deep\u201d

(57:33) Using flashtags to communicate opinions

(01:02:44) HubSpot\u2019s 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:

\u2022 WordPlay: https://wordplay.com/article/unlimited

\u2022 ChatSpot: https://chatspot.ai/

\u2022 Indian-origin entrepreneur buys \u2018chat.com\u2019 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

\u2022 Kipp Bodnar on LinkedIn: https://www.linkedin.com/in/kippbodnar/

\u2022 The surprising metric presenters should analyze: https://lars-sudmann.com/the-surprising-metric-presenters-should-analyze/

\u2022 SoloWare: https://www.linkedin.com/posts/dharmesh_for-3-decades-now-in-addition-to-my-day-activity-7166500611247583232-kZgb/

\u2022 Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan/

\u2022 First Principles: Elon Musk on the Power of Thinking for Yourself: https://jamesclear.com/first-principles

\u2022 Peter Thiel on LinkedIn: https://www.linkedin.com/in/peterthiel/

\u2022 The second law of thermodynamics: https://en.wikipedia.org/wiki/Second_law_of_thermodynamics

\u2022 What is an SMB?: https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business

\u2022 Shopify: https://www.shopify.com/

\u2022 Relentless curiosity, radical accountability, and HubSpot\u2019s 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/

\u2022 FlashTags: A Simple Hack for Conveying Context Without Confusion: https://www.onstartups.com/flashtags-a-simple-hack-for-conveying-context-without-confusion

\u2022 What it means to \u201cdisagree and commit\u201d: https://news.ycombinator.com/item?id=16949021

\u2022 A Simple Decision Framework: Debate, Decide and Unite: https://connectingdots.com/p/debate-decide-unite

\u2022 Dharmesh Shah\u2019s Frameworks for Creating a $1 Billion Net Worth: https://hakune.co/dharmesh-shah-networth/

\u2022 Zip: https://ziphq.com/

\u2022 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

\u2022 How defining values and culture helped Airbnb achieve worldwide success: https://lattice.com/library/how-defining-values-and-culture-helped-airbnb-achie

\u2022 What is SQL?: https://aws.amazon.com/what-is/sql/

\u2022 GrowthBot: https://community.hubspot.com/t5/Releases-and-Updates/Meet-GrowthBot-from-HubSpot-Labs/ba-p/417985

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.