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

ℹ️ EPISODE INFO

Released

April 4, 2024

Duration

1h 41m

Channel

Lenny's Podcast

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

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 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 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.

🎤 SPEAKERS

• Dharmesh Shah

  guest

• Lenny Rachitsky

  host

• Narrator

  other

🧾 EPISODE SUMMARY

In this episode of Lenny's Podcast, featuring Dharmesh Shah and Lenny Rachitsky, Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO) explores dharmesh Shah on contrarian culture, simplicity, AI, and no managers HubSpot co-founder and CTO Dharmesh Shah shares how he’s deliberately built a $30B company in highly unconventional ways: no direct reports, radical transparency, and a broad all‑in‑one product from day one. He explains his systems-first approach to public speaking (including measuring laughs per minute), decision-making, and culture-building, treating culture as a product to be iterated rather than preserved. Dharmesh dives into why HubSpot stayed focused on SMB despite intense pressure to move upmarket, how to fight organizational entropy with simplicity, and how to zig when everyone else zags. He closes with his views on AI as “cognition at scale,” the future of declarative interfaces, and a practical framework for choosing what ideas to pursue.

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