Lenny's Podcast: Product | Career | Growth

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

April 4, 2024

AI Summary

5 min read

Dharmesh Shah, co-founder and CTO of HubSpot, shares how he and his co-founder structured the company around contrarian choices like focusing solely on SMB customers, building a broad all-in-one product from day one, and experimenting with flat structures, while emphasizing simplicity to combat growing complexity.

Focusing on strengths and avoiding management
Shah never took direct reports at HubSpot, a decision made in the first founders' meeting to avoid becoming "passively okay" at management through years of effort. He invests instead in areas of natural strength, like building SoloWare—personal tools such as LPM (laughs per minute) software for keynote practice, which measures audience laughter via transcripts and recordings to iteratively improve humor delivery. This approach lets him enjoy scale's upsides, like big bets, without management downsides, and he applies similar logic to company rules, such as no meetings before 11 a.m. unless excluding co-founders.

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What you'll learn

1 **[04:15] Fun facts & personal background**
2 **[00:07:33] Mastering public speaking via LPM metric**
3 **[15:28] No direct reports & leaning into strengths**
4 **[20:13] Public company lessons & radical transparency**
5 **[27:36] Contrarian bets: SMB focus, no titles, seat lottery**
6 **[37:42] Fighting entropy: simplicity as operating principle**
7 **[50:52] Zig vs. zag: broad all-in-one product for SMB**

+ Full timestamped outline available in the app

Show Notes

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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