<description>&lt;p&gt;&lt;strong&gt;Dharmesh Shah&lt;/strong&gt; 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 &lt;a target="_blank" href="http://onstartups.com/"&gt;OnStartups&lt;/a&gt;, 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:&lt;/p&gt;&lt;p&gt;• The biggest lessons he has learned from building HubSpot&lt;/p&gt;&lt;p&gt;• The importance of leaning into your strengths&lt;/p&gt;&lt;p&gt;• Dharmesh’s data-oriented approach to public speaking&lt;/p&gt;&lt;p&gt;• How he developed HubSpot’s culture code&lt;/p&gt;&lt;p&gt;• The decision-making process at HubSpot&lt;/p&gt;&lt;p&gt;• His contrarian approach to building products&lt;/p&gt;&lt;p&gt;• Why founders and product teams are all fighting the second law of thermodynamics&lt;/p&gt;&lt;p&gt;• How “flash tags” can save your teams time&lt;/p&gt;&lt;p&gt;• How to decide what ideas are worth investing in&lt;/p&gt;&lt;p&gt;—&lt;/p&gt;&lt;p&gt;&lt;strong&gt;Brought to you by:&lt;/strong&gt;&lt;/p&gt;&lt;p&gt;• &lt;a target="_blank" href="https://explo.co/lenny"&gt;Explo&lt;/a&gt;—Embed customer-facing analytics in your product&lt;/p&gt;&lt;p&gt;• &lt;a target="_blank" href="https://vanta.com/lenny"&gt;Vanta&lt;/a&gt;—Automate compliance. Simplify security&lt;/p&gt;&lt;p&gt;• &lt;a target="_blank" href="https://www.linkedin.com/podlenny"&gt;LinkedIn Ads&lt;/a&gt;—Reach professionals and drive results for your business&lt;/p&gt;&lt;p&gt;—&lt;/p&gt;&lt;p&gt;&lt;strong&gt;Find the full transcript at: &lt;/strong&gt;&lt;a target="_blank" href="https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building"&gt;https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building&lt;/a&gt;&lt;/p&gt;&lt;p&gt;—&lt;/p&gt;&lt;p&gt;&lt;strong&gt;Where to find Dharmesh Shah:&lt;/strong&gt;&lt;/p&gt;&lt;p&gt;• X: &lt;a target="_blank" href="https://twitter.com/dharmesh"&gt;https://twitter.com/dharmesh&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• LinkedIn: &lt;a target="_blank" href="https://www.linkedin.com/in/dharmesh/"&gt;https://www.linkedin.com/in/dharmesh/&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• Website: &lt;a target="_blank" href="https://dharmesh.com/"&gt;https://dharmesh.com/&lt;/a&gt;&lt;/p&gt;&lt;p&gt;—&lt;/p&gt;&lt;p&gt;&lt;strong&gt;Where to find Lenny:&lt;/strong&gt;&lt;/p&gt;&lt;p&gt;• Newsletter: &lt;a target="_blank" href="https://www.lennysnewsletter.com"&gt;https://www.lennysnewsletter.com&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• X: &lt;a target="_blank" href="https://twitter.com/lennysan"&gt;https://twitter.com/lennysan&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• LinkedIn: &lt;a target="_blank" href="https://www.linkedin.com/in/lennyrachitsky/"&gt;https://www.linkedin.com/in/lennyrachitsky/&lt;/a&gt;&lt;/p&gt;&lt;p&gt;—&lt;/p&gt;&lt;p&gt;&lt;strong&gt;In this episode, we cover:&lt;/strong&gt;&lt;/p&gt;&lt;p&gt;(00:00) Dharmesh’s background&lt;/p&gt;&lt;p&gt;(04:20) Fun facts about Dharmesh&lt;/p&gt;&lt;p&gt;(06:31) His data-oriented approach to public speaking&lt;/p&gt;&lt;p&gt;(11:45) Advice for adding humor to your presentations&lt;/p&gt;&lt;p&gt;(15:28) Why he has no direct reports&lt;/p&gt;&lt;p&gt;(18:46) You can shape the universe to your liking&lt;/p&gt;&lt;p&gt;(20:02) Lessons from building HubSpot&lt;/p&gt;&lt;p&gt;(23:43) Contrarian ways of running a company&lt;/p&gt;&lt;p&gt;(37:26) Fighting the second law of thermodynamics &lt;/p&gt;&lt;p&gt;(40:29) The importance of simplicity in running a business&lt;/p&gt;&lt;p&gt;(45:22) Succeeding in the SMB market&lt;/p&gt;&lt;p&gt;(50:29) Zigging when others are zagging&lt;/p&gt;&lt;p&gt;(54:17) When it makes sense to go “wide and deep”&lt;/p&gt;&lt;p&gt;(57:33) Using flashtags to communicate opinions&lt;/p&gt;&lt;p&gt;(01:02:44) HubSpot’s decision-making process &lt;/p&gt;&lt;p&gt;(01:09:41) Deciding what ideas to invest in&lt;/p&gt;&lt;p&gt;(01:15:26) Defining and maintaining company culture&lt;/p&gt;&lt;p&gt;(01:30:46) The potential of AI&lt;/p&gt;&lt;p&gt;(01:37:03) Practical advice for learning AI&lt;/p&gt;&lt;p&gt;(01:40:07) Where to find Dharmesh&lt;/p&gt;&lt;p&gt;—&lt;/p&gt;&lt;p&gt;&lt;strong&gt;Referenced:&lt;/strong&gt;&lt;/p&gt;&lt;p&gt;• WordPlay: &lt;a target="_blank" href="https://wordplay.com/article/unlimited"&gt;https://wordplay.com/article/unlimited&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• ChatSpot: &lt;a target="_blank" href="https://chatspot.ai/"&gt;https://chatspot.ai/&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• Indian-origin entrepreneur buys ‘chat.com’ for over $10 million, then sells, donates $250,000 to Khan Academy: &lt;a target="_blank" href="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"&gt;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&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• Kipp Bodnar on LinkedIn: &lt;a target="_blank" href="https://www.linkedin.com/in/kippbodnar/"&gt;https://www.linkedin.com/in/kippbodnar/&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• The surprising metric presenters should analyze: &lt;a target="_blank" href="https://lars-sudmann.com/the-surprising-metric-presenters-should-analyze/"&gt;https://lars-sudmann.com/the-surprising-metric-presenters-should-analyze/&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• SoloWare: &lt;a target="_blank" href="https://www.linkedin.com/posts/dharmesh_for-3-decades-now-in-addition-to-my-day-activity-7166500611247583232-kZgb/"&gt;https://www.linkedin.com/posts/dharmesh_for-3-decades-now-in-addition-to-my-day-activity-7166500611247583232-kZgb/&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• Brian Halligan on LinkedIn: &lt;a target="_blank" href="https://www.linkedin.com/in/brianhalligan/"&gt;https://www.linkedin.com/in/brianhalligan/&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• First Principles: Elon Musk on the Power of Thinking for Yourself: &lt;a target="_blank" href="https://jamesclear.com/first-principles"&gt;https://jamesclear.com/first-principles&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• Peter Thiel on LinkedIn: &lt;a target="_blank" href="https://www.linkedin.com/in/peterthiel/"&gt;https://www.linkedin.com/in/peterthiel/&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• The second law of thermodynamics: &lt;a target="_blank" href="https://en.wikipedia.org/wiki/Second_law_of_thermodynamics"&gt;https://en.wikipedia.org/wiki/Second_law_of_thermodynamics&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• What is an SMB?: &lt;a target="_blank" href="https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business"&gt;https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• Shopify: &lt;a target="_blank" href="https://www.shopify.com/"&gt;https://www.shopify.com/&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• Relentless curiosity, radical accountability, and HubSpot’s winning growth formula | Christopher Miller (VP of Product, Growth and AI): &lt;a target="_blank" href="https://www.lennyspodcast.com/relentless-curiosity-radical-accountability-and-hubspots-winning-growth-formula-christopher-mil/"&gt;https://www.lennyspodcast.com/relentless-curiosity-radical-accountability-and-hubspots-winning-growth-formula-christopher-mil/&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• FlashTags: A Simple Hack for Conveying Context Without Confusion: &lt;a target="_blank" href="https://www.onstartups.com/flashtags-a-simple-hack-for-conveying-context-without-confusion"&gt;https://www.onstartups.com/flashtags-a-simple-hack-for-conveying-context-without-confusion&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• What it means to “disagree and commit”: &lt;a target="_blank" href="https://news.ycombinator.com/item?id=16949021"&gt;https://news.ycombinator.com/item?id=16949021&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• A Simple Decision Framework: Debate, Decide and Unite: &lt;a target="_blank" href="https://connectingdots.com/p/debate-decide-unite"&gt;https://connectingdots.com/p/debate-decide-unite&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• Dharmesh Shah’s Frameworks for Creating a $1 Billion Net Worth: &lt;a target="_blank" href="https://hakune.co/dharmesh-shah-networth/"&gt;https://hakune.co/dharmesh-shah-networth/&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• Zip: &lt;a target="_blank" href="https://ziphq.com/"&gt;https://ziphq.com/&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• The HubSpot Culture Code: Creating a Company We Love: &lt;a target="_blank" href="https://blog.hubspot.com/blog/tabid/6307/bid/34234/the-hubspot-culture-code-creating-a-company-we-love.aspx"&gt;https://blog.hubspot.com/blog/tabid/6307/bid/34234/the-hubspot-culture-code-creating-a-company-we-love.aspx&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• How defining values and culture helped Airbnb achieve worldwide success: &lt;a target="_blank" href="https://lattice.com/library/how-defining-values-and-culture-helped-airbnb-achie"&gt;https://lattice.com/library/how-defining-values-and-culture-helped-airbnb-achie&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• What is SQL?: &lt;a target="_blank" href="https://aws.amazon.com/what-is/sql/"&gt;https://aws.amazon.com/what-is/sql/&lt;/a&gt;&lt;/p&gt;&lt;p&gt;• GrowthBot: &lt;a target="_blank" href="https://community.hubspot.com/t5/Releases-and-Updates/Meet-GrowthBot-from-HubSpot-Labs/ba-p/417985"&gt;https://community.hubspot.com/t5/Releases-and-Updates/Meet-GrowthBot-from-HubSpot-Labs/ba-p/417985&lt;/a&gt;&lt;/p&gt;&lt;p&gt;—&lt;/p&gt;&lt;p&gt;Production and marketing by &lt;a target="_blank" href="https://penname.co/"&gt;https://penname.co/&lt;/a&gt;. For inquiries about sponsoring the podcast, email &lt;a target="_blank" href="mailto:podcast@lennyrachitsky.com"&gt;podcast@lennyrachitsky.com&lt;/a&gt;.&lt;/p&gt;&lt;p&gt;—&lt;/p&gt;&lt;p&gt;&lt;em&gt;Lenny may be an investor in the companies discussed.&lt;/em&gt;&lt;/p&gt; &lt;br/&gt;&lt;br/&gt;Get full access to Lenny's Newsletter at &lt;a href="https://www.lennysnewsletter.com/subscribe?utm_medium=podcast&amp;#38;utm_campaign=CTA_4"&gt;www.lennysnewsletter.com/subscribe&lt;/a&gt;</description>

Lenny's Podcast: Product | Growth | Career

Lenny Rachitsky

Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO)

APR 4, 2024101 MIN
Lenny's Podcast: Product | Growth | Career

Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO)

APR 4, 2024101 MIN

Description

<p><strong>Dharmesh Shah</strong> 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 <a target="_blank" href="http://onstartups.com/">OnStartups</a>, 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:</p><p>• The biggest lessons he has learned from building HubSpot</p><p>• The importance of leaning into your strengths</p><p>• Dharmesh’s data-oriented approach to public speaking</p><p>• How he developed HubSpot’s culture code</p><p>• The decision-making process at HubSpot</p><p>• His contrarian approach to building products</p><p>• Why founders and product teams are all fighting the second law of thermodynamics</p><p>• How “flash tags” can save your teams time</p><p>• How to decide what ideas are worth investing in</p><p>—</p><p><strong>Brought to you by:</strong></p><p>• <a target="_blank" href="https://explo.co/lenny">Explo</a>—Embed customer-facing analytics in your product</p><p>• <a target="_blank" href="https://vanta.com/lenny">Vanta</a>—Automate compliance. Simplify security</p><p>• <a target="_blank" href="https://www.linkedin.com/podlenny">LinkedIn Ads</a>—Reach professionals and drive results for your business</p><p>—</p><p><strong>Find the full transcript at: </strong><a target="_blank" href="https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building">https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building</a></p><p>—</p><p><strong>Where to find Dharmesh Shah:</strong></p><p>• X: <a target="_blank" href="https://twitter.com/dharmesh">https://twitter.com/dharmesh</a></p><p>• LinkedIn: <a target="_blank" href="https://www.linkedin.com/in/dharmesh/">https://www.linkedin.com/in/dharmesh/</a></p><p>• Website: <a target="_blank" href="https://dharmesh.com/">https://dharmesh.com/</a></p><p>—</p><p><strong>Where to find Lenny:</strong></p><p>• Newsletter: <a target="_blank" href="https://www.lennysnewsletter.com">https://www.lennysnewsletter.com</a></p><p>• X: <a target="_blank" href="https://twitter.com/lennysan">https://twitter.com/lennysan</a></p><p>• LinkedIn: <a target="_blank" href="https://www.linkedin.com/in/lennyrachitsky/">https://www.linkedin.com/in/lennyrachitsky/</a></p><p>—</p><p><strong>In this episode, we cover:</strong></p><p>(00:00) Dharmesh’s background</p><p>(04:20) Fun facts about Dharmesh</p><p>(06:31) His data-oriented approach to public speaking</p><p>(11:45) Advice for adding humor to your presentations</p><p>(15:28) Why he has no direct reports</p><p>(18:46) You can shape the universe to your liking</p><p>(20:02) Lessons from building HubSpot</p><p>(23:43) Contrarian ways of running a company</p><p>(37:26) Fighting the second law of thermodynamics </p><p>(40:29) The importance of simplicity in running a business</p><p>(45:22) Succeeding in the SMB market</p><p>(50:29) Zigging when others are zagging</p><p>(54:17) When it makes sense to go “wide and deep”</p><p>(57:33) Using flashtags to communicate opinions</p><p>(01:02:44) HubSpot’s decision-making process </p><p>(01:09:41) Deciding what ideas to invest in</p><p>(01:15:26) Defining and maintaining company culture</p><p>(01:30:46) The potential of AI</p><p>(01:37:03) Practical advice for learning AI</p><p>(01:40:07) Where to find Dharmesh</p><p>—</p><p><strong>Referenced:</strong></p><p>• WordPlay: <a target="_blank" href="https://wordplay.com/article/unlimited">https://wordplay.com/article/unlimited</a></p><p>• ChatSpot: <a target="_blank" href="https://chatspot.ai/">https://chatspot.ai/</a></p><p>• Indian-origin entrepreneur buys ‘chat.com’ for over $10 million, then sells, donates $250,000 to Khan Academy: <a target="_blank" href="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">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</a></p><p>• Kipp Bodnar on LinkedIn: <a target="_blank" href="https://www.linkedin.com/in/kippbodnar/">https://www.linkedin.com/in/kippbodnar/</a></p><p>• The surprising metric presenters should analyze: <a target="_blank" href="https://lars-sudmann.com/the-surprising-metric-presenters-should-analyze/">https://lars-sudmann.com/the-surprising-metric-presenters-should-analyze/</a></p><p>• SoloWare: <a target="_blank" href="https://www.linkedin.com/posts/dharmesh_for-3-decades-now-in-addition-to-my-day-activity-7166500611247583232-kZgb/">https://www.linkedin.com/posts/dharmesh_for-3-decades-now-in-addition-to-my-day-activity-7166500611247583232-kZgb/</a></p><p>• Brian Halligan on LinkedIn: <a target="_blank" href="https://www.linkedin.com/in/brianhalligan/">https://www.linkedin.com/in/brianhalligan/</a></p><p>• First Principles: Elon Musk on the Power of Thinking for Yourself: <a target="_blank" href="https://jamesclear.com/first-principles">https://jamesclear.com/first-principles</a></p><p>• Peter Thiel on LinkedIn: <a target="_blank" href="https://www.linkedin.com/in/peterthiel/">https://www.linkedin.com/in/peterthiel/</a></p><p>• The second law of thermodynamics: <a target="_blank" href="https://en.wikipedia.org/wiki/Second_law_of_thermodynamics">https://en.wikipedia.org/wiki/Second_law_of_thermodynamics</a></p><p>• What is an SMB?: <a target="_blank" href="https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business">https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business</a></p><p>• Shopify: <a target="_blank" href="https://www.shopify.com/">https://www.shopify.com/</a></p><p>• Relentless curiosity, radical accountability, and HubSpot’s winning growth formula | Christopher Miller (VP of Product, Growth and AI): <a target="_blank" href="https://www.lennyspodcast.com/relentless-curiosity-radical-accountability-and-hubspots-winning-growth-formula-christopher-mil/">https://www.lennyspodcast.com/relentless-curiosity-radical-accountability-and-hubspots-winning-growth-formula-christopher-mil/</a></p><p>• FlashTags: A Simple Hack for Conveying Context Without Confusion: <a target="_blank" href="https://www.onstartups.com/flashtags-a-simple-hack-for-conveying-context-without-confusion">https://www.onstartups.com/flashtags-a-simple-hack-for-conveying-context-without-confusion</a></p><p>• What it means to “disagree and commit”: <a target="_blank" href="https://news.ycombinator.com/item?id=16949021">https://news.ycombinator.com/item?id=16949021</a></p><p>• A Simple Decision Framework: Debate, Decide and Unite: <a target="_blank" href="https://connectingdots.com/p/debate-decide-unite">https://connectingdots.com/p/debate-decide-unite</a></p><p>• Dharmesh Shah’s Frameworks for Creating a $1 Billion Net Worth: <a target="_blank" href="https://hakune.co/dharmesh-shah-networth/">https://hakune.co/dharmesh-shah-networth/</a></p><p>• Zip: <a target="_blank" href="https://ziphq.com/">https://ziphq.com/</a></p><p>• The HubSpot Culture Code: Creating a Company We Love: <a target="_blank" href="https://blog.hubspot.com/blog/tabid/6307/bid/34234/the-hubspot-culture-code-creating-a-company-we-love.aspx">https://blog.hubspot.com/blog/tabid/6307/bid/34234/the-hubspot-culture-code-creating-a-company-we-love.aspx</a></p><p>• How defining values and culture helped Airbnb achieve worldwide success: <a target="_blank" href="https://lattice.com/library/how-defining-values-and-culture-helped-airbnb-achie">https://lattice.com/library/how-defining-values-and-culture-helped-airbnb-achie</a></p><p>• What is SQL?: <a target="_blank" href="https://aws.amazon.com/what-is/sql/">https://aws.amazon.com/what-is/sql/</a></p><p>• GrowthBot: <a target="_blank" href="https://community.hubspot.com/t5/Releases-and-Updates/Meet-GrowthBot-from-HubSpot-Labs/ba-p/417985">https://community.hubspot.com/t5/Releases-and-Updates/Meet-GrowthBot-from-HubSpot-Labs/ba-p/417985</a></p><p>—</p><p>Production and marketing by <a target="_blank" href="https://penname.co/">https://penname.co/</a>. For inquiries about sponsoring the podcast, email <a target="_blank" href="mailto:[email protected]">[email protected]</a>.</p><p>—</p><p><em>Lenny may be an investor in the companies discussed.</em></p> <br/><br/>Get full access to Lenny's Newsletter at <a href="https://www.lennysnewsletter.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_4">www.lennysnewsletter.com/subscribe</a>