The Orbit Shift Podcast

S01E10: Slack Co-Founder & CTO Cal Henderson & Freshworks CEO Girish Mathrubootham discuss leadership, failure, side projects and success


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Twenty years ago, Cal Henderson was working in London while Stewart Butterfield was making a game called Game Neverending. Henderson, a big fan of the game, broke into the email server to join the internal mailing list of Butterfield’s 4 person company. Eventually, Cal convinced Butterfield to hire him.  The game was not going anywhere, so they started focusing on a side project which eventually became Flickr and eventually sold to Yahoo in 2005. The two founders went back to building another gaming company called Glitch. That didn’t do well either. Another side project, that helped Glitch manage their remote teams now became the core product. They called it Slack. And the rest is history.  Today Slack has a market cap of almost $15 billion. In the quarter ended April 2020, it pulled in over $200 million in revenues, growing at 49% compared to the year-ago quarter, with a gross margin of 87.3% and a stellar net retention rate of 132%.
This episode of The Orbit Shift Podcast brings you a fireside chat between Cal Henderson and Girish Mathrubootham. The two talked about 
🚀Achieving Product-market fit

🚀Convincing others to use Slack

🚀Growing beyond the original product-market fit

🚀The #2 reason why startups fail

🚀Success comes from failure

🚀Giving away your lego blocks 

🚀Go from sprinting to running a marathon

🚀Stress and the role of leaders 

🚀Succeeding in the post-Covid world

This episode was originally recorded as part of the AgainstAllOdds startup summit conducted by Freshworks for Startups. 

Get $10,000 free credits to use Freshworks products by joining the Freshworks for Startups program. Click here to check eligibility. 


About the Guest

Cal Henderson is the co-founder and CTO of Slack. Previously, Cal built and led the engineering teams at Flickr, until its acquisition by Yahoo. An experienced technology leader and a popular speaker on engineering scalability, he authored the best-selling O’Reilly Media book Building Scalable Websites. Cal was also a pioneer in the use of web APIs and created the basis for OAuth and oEmbed, now used by YouTube, Twitter and many others. He has a Bachelor of Computer Science and has received an Honorary Doctorate from Birmingham City University. He now resides in San Francisco.


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The Orbit Shift Podcast is Powered by Freshworks Inc. a global SaaS company headquartered in San Mateo, California. 


Host and Producer - Jayadevan PK

Assistant Producer - Shashwath J

Audio Engineer - Rajesh Subramanian

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The Orbit Shift PodcastBy Freshworks Inc.