Leadership and Humor in Public Speaking

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.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe