Series A from Tiger Global and fundraising lessons

Sid Yadav is the Co-founder and CEO of Circle, the all-in-one community platform trusted by creators like Tiago Forte, David Perell, and Miles Snider. Sid started the tech blog Rev2 when he was a teenager in New Zealand, writing about the launch of YouTube and the iPhone. He was the founding engineer and designer of Teachable, which he helped scale to +25m+ in ARR before it was acquired in 2020. He started Circle in 2019 with co-founders Rudy Santino and Andrew Guttormsen, which they scaled to $16m in ARR by December of 2023.

Circle has since raised $31m from Investors like Tiger Global, Notation Capital, Bungalow, Todd Goldberg, Rahul Vohra, Scott Belsky, Josh Buckley, Ankur Nagpal, Wade Foster, and Dharmesh Shah.

Sid immigrated with his family from India to New Zealand as a teenager and to the US after college. His story is a perfect encapsulation of the American Dream, and I’m excited to share this conversation.

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Topics discussed include:

• (03:53) Why the creator economy is booming despite negative sentiment

• (13:22) Writing a popular tech blog as a teen in the mid 00’s

• (23:16) Joining Teachable as the 2nd employee

• (40:30) Why Teachable CEO Ankur Nagpal invested 90% of his liquid net worth in Circle’s $1.7m Pre-seed round

• (48:44) Sid’s inside view at the creator economy before, during, and after COVID

• (52:50) The magic of Lenny Rachitsky’s creator flywheel

• (56:10) The reason Sid raised a Seed from lots of investors instead of one large check

• (01:14:30) Inside raising a Series A from Tiger Global in 2021

• (01:22:19) Why Sid writes an investor update every month

• (01:25:15) Going from Zero to $16m ARR in four years

• (01:27:28) How Circle approaches its product roadmap

• (01:29:20) Building a community around your product

• (01:37:03) Advice for running a remote-first team

• (01:46:54) How Sid convinced the founder of Zapier to be his CEO coach

• (01:54:20) Why founders need to deal with reality

Referenced:

https://circle.so/

https://www.teachable.com

“Cost of a meeting” tweet: https://twitter.com/0xgaut/status/1620815168921038850

Tiago Forte Building a Second Brain: https://www.buildingasecondbrain.com/foundation

PARA Method: https://fortelabs.com/blog/para/

Lenny’s interview with Brian Chesky: https://www.youtube.com/watch?v=4ef0juAMqoE

Turner’s interview with Wade Foster, Co-founder and CEO of Zapier:  https://youtu.be/NJMjuYt9jEc

Myles Snyder: https://mylessnider.com/

Where to find Sid:

• Twitter: https://twitter.com/sidyadav
• LinkedIn: https://www.linkedin.com/in/sidyadav

Where to find Turner:

• Newsletter: https://www.thespl.it
• Twitter: https://twitter.com/TurnerNovak
• Banana Capital: https://bananacapital.vc