Surviving Two Seed Extensions, Fixing Auth for AI Agents | Clerk Founder & CEO Colin Sidoti
The Peel with Turner Novak
Turner Novak
4.6 • 11 Ratings
🗓️ 17 April 2025
⏱️ 100 minutes
🧾️ Download transcript
Summary
Colin Sidoti is the Co-founder and CEO of Clerk, the best way to build authentication and user management.
I loved this conversation, because Colin is currently in the arena building Clerk. It has not been easy, and he takes us inside some of the harder moments of the past six years.
We hit on three main themes: authentication; lessons raising multiple hard Seed extensions in the early days, including a recap before the A, and the demo that got a16z to invest; and things AI and MCP.
We also talk founding a company with his brother, building a compound startup, why components are the new APIs, and what he learned about audacious goals from John Collison @ Stripe
A big thank you to Reid Christian @ CRV, Paul Klein @ Browserbase, and Joseph Nelson @ Roboflow for helping brainstorm topics for Colin.
Timestamps:
(3:39) The best developer tool for authentication and user management
(5:45) The easiest way to set up billing
(7:13) Building a compound startup
(9:15) Lesson on audacious goals from John Collison
(12:40) Developer tools are now trusted category experts
(13:47) How auth impacts billing, CRM, marketing, analytics
(19:44) Why auth is always changing
(25:40) Coming up with the idea for Clerk
(29:24) What its like starting a company with your brother
(30:58) Living in a basement during Clerks early days
(35:33) Getting early users narrowing focus in South Park Commons
(40:10) Fundraising lessons from struggling to raise
(43:46) The trick that raised Clerk’s first round from S28
(45:09) Launching + the first Seed extension
(50:15) Sequoia’s feedback that improved conversion rates
(52:22) Why a16z led Clerk’s 2nd Seed extension
(58:11) How to do a recap before Series A
(1:03:34) Changing Clerk’s pitch to scare investors
(1:08:56) Fundraising advice “Why partner alignment is all that matters”
(1:11:42) Fast Series A and breaking 7%/week growth
(1:16:32) Negotiating Clerk’s Series B at the bar
(1:22:15) Investors in the arena vs in their mansions
(1:27:57) The three ways AI is changing authentication
(1:31:21) Why AI agents all try to steal free AI credits
(1:33:09) Remember to have fun
(1:36:24) Building a better product to compete in a crowded market
Referenced
Try Clerk: https://clerk.com/
Jobs at Clerk: https://clerk.com/careers
Martin Casado’s tweet https://x.com/martin_casado/status/1558134697753841664
Try Inngest: https://www.inngest.com/
Follow Colin
Twitter: https://x.com/tweetsbycolin
LinkedIn: https://www.linkedin.com/in/colin-sidoti-751a219
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Transcript
Click on a timestamp to play from that location
| 0:00.0 | Look at your onboarding. |
| 0:01.5 | How many steps is it? |
| 0:02.8 | How can you get rid of a step? |
| 0:04.2 | If I were to characterize all of Clark's lifetime, like, that's what we've been doing, |
| 0:08.4 | is just how do we take steps away? |
| 0:11.0 | And we pitched Sequoia early on in the seed. |
| 0:16.2 | And I actually really liked the feedback. |
| 0:18.9 | They came back and said, Stripe took this many week process and |
| 0:23.6 | turned it into hours. And Twilio did the same thing. And like, we just don't know if taking hours, |
| 0:33.0 | which is what kind of off was at, taking it down to minutes if people are really going to care. |
| 0:39.5 | And that was what they relayed when they passed. |
| 0:42.6 | And we didn't know either. |
| 0:43.7 | And I really appreciated that feedback because it was like, you thought about it, right? |
| 0:47.6 | But we've always had this belief that like if we just take the onboarding steps and we just try to remove steps one by one, |
| 0:52.9 | we'll just be the fastest |
| 0:54.2 | way to set things up. And developers are just like ruthless about how efficient can I be. |
| 1:00.9 | That process just made the onboarding that much easier. And that's ultimately where things |
| 1:07.5 | started to pull. Welcome to the Peel. I'm your host, Turner Novak, founder of Banana Capital. |
| 1:12.6 | Today's guest is Colin Sedoti, co-founder and CEO of Clerk. |
| 1:16.6 | Developer tools for authentication, sign up, sign in, user profile, |
| 1:20.6 | and you can just drop them on your app and they'll work. |
| 1:24.6 | I love this conversation because Colin is currently in the arena building clerk. |
... |
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