🎧🍌 Surviving Two Seed Extensions, Fixing Auth for AI Agents | Clerk Founder & CEO Colin Sidoti
How to recap a Seed stage company, leveraging Associates when fundraising, why you shouldn't change your pitch for investors, building a compound startup, why AI agents are stealing free AI credits
Colin started Clerk with his brother Braden in 2019. He’s tweeted charts like the one below (missing the first two years) showing their impressive growth, but it has not been an easy journey.
Colin takes us inside the hardest moments from the past six years, including lessons raising two hard Seed extensions and recapping the company before their Series A.
We hit on three main themes: authentication, fundraising, and how AI and MCP intersect with auth.
We also get into what it’s like 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.
Colin was very open and transparent throughout this conversation. If you’re interested in getting in the weeds of early stage fundraising tactics from someone in the arena, you’ll love this one.
A big thank you to Reid Christian @ CRV, and prior guests of the show Paul Klein IV @ Browserbase and Joseph Nelson @ Roboflow for their help brainstorm topics for Colin.
Timestamps to jump in:
3:39 Clerk: the best authentication and user management platform
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 friends basement in Clerk’s early days
35:33 Narrowing focus at 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 Recapping the company before the Series A
1:03:34 Changing Clerk’s pitch to scare investors
1:08:56 “Why partner alignment is all that matters”
1:11:42 The 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:
Find Colin on X / Twitter and LinkedIn
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Transcript - (read on Rev)
Find transcripts of all prior episodes here.
Turner Novak:
Colin, welcome to the show.
Colin Sidoti:
Thanks for having me.
Turner Novak:
Yeah, I think this will be fun. We had an interesting, I guess, way we connected on this with a prior guest of the show. You tweeted something about a clip that we posted, which I think you said was your most viral tweet ever.
Colin Sidoti:
I think it was. Yeah. And now I'm on the show. So I guess a successful tweet.
Turner Novak:
Yeah. So real quick, for people who don't know, what is Clerk?
Colin Sidoti:
So Clerk is developer tools for authentication is the easiest way to think about it. We make React components, like sign up, sign in, user profile, and you can just drop them on your app and they'll work. And then we also help with the B2B side of onboarding. So tell us what your team name is, invite your teammates, and set their role and permissions. And so, we help app developers build those parts of their application.
Turner Novak:
This is kind of a thing that everyone needs to do, but it's always been something that you just hacked together, historically?
Colin Sidoti:
In a sense, yeah. I mean, there's always been, I think depending on your stack, there's always been Rails had Devise and Node for a long time was Passport. And I think a big way Clerk found our footing was auth for React. And so, even the way I just pitched it there was the sign in component, sign up component, user profile component. Yeah.
Turner Novak:
That's Clerk.
Colin Sidoti:
That's Clerk.
Turner Novak:
So I think an interesting question that'll open up some other angles, what does Clerk mean? Why did you pick that name?
Colin Sidoti:
Yeah, so despite how I just pitched it, I guess Clerk has a much broader vision. And I think the core insight, first of all, my brother and I founded it, and I think the core insight we had back in 2019 was if you look at any software companies, code around their user object, so not just the sign-in stuff, but after someone signed in, what are you doing with the user data, you're normally syncing it and sending it to a standard set of people.
So Stripe needs it to be able to do billing, and your CRM needs it to be able to keep track of accounts, and your marketing tools need it, and analytics tools need it, and the list kind of goes on and on. And that piece or block of code is duplicated across every startup in the world. And so we basically approach the problem as like, can we do auth in a way where one day we'll be able to add a billing service, add a CRM service, add an analytics service? And now we're at the point where we're doing that.
Turner Novak:
You're kind of doing that, right? Yeah.
Colin Sidoti:
Yes. So depending on when this launches, billing will either be out or in private data. But we actually got Stripe to invest in our series B and we've got a good partnership there, where Clerk's going to launch a billing feature and it'll use Stripe payments, but it should be the easiest DX to set up billing for your application.
Turner Novak:
So is it just copy and paste some code and we're good to go? Is it that easy?
Colin Sidoti:
Yeah, that's the intent. And we're adding a pricing table component. If you think about it, we already have the real estate that billing normally lives in. It's normally in your user profile or your organization profile is where you'd go to change your plan.
Turner Novak:
As a customer or user of software?
Colin Sidoti:
Exactly. Yeah. So on GitHub, what plan am I on? You go to your user profile and you go to the billing tab. And so, we already offer people the user profile, and they go and they set their 2FA there, they change their profile image, whatever, and we're just adding a billing tab. So we already have that real estate. And we have to add a pricing table, which is the entry point to first subscribing to a plan.
Turner Novak:
Talking about tweets, you tweeted something about compound startups, which is basically there's a lot of different things that you do. I think some people say you should do one thing that's super simple. Some people say you should do a bunch of different things. How do you think about that with Clerk?
Colin Sidoti:
I think we should do a lot of things. I mean, so to me, the person who coined this phrase is Parker Conrad.
Turner Novak:
Parker Conrad.
Colin Sidoti:
Rippling. I failed to remember his name for a second there.
Turner Novak:
He's also in the news cycle right now with some other crazy stuff.
Colin Sidoti:
Yes. We can maybe jump to that. But yeah, so I think for identity in particular, building a compound startup makes a lot of sense because... So Rippling has employee identity, and they start with payroll, and they're able to add applicant tracking, and benefits, and IT, and just product after product that surrounds the employee identity. Clerk is very much the same way. We do sign up, so we have customer identity, and Stripe billing. You don't just charge, you charge a user. And for email, you don't just send emails, you email your users.
And so all these things are very strongly coupled to identity, and that's why we think we can improve the DX around them, and the UX. And this is a big piece that Rippling talks about is one of their big advantages is that they get to have a common through line of user experience through all of these different services. And for Clerk, it's the same way, both dashboard side for people administering it, but also front end side. If you give us customization variables to tweak user profile and sign in, those will also apply to billing. So we get to provide a consistent UX to your users.
Turner Novak:
Yeah. So I think another maybe lesson that you've learned is just the power of audacious goals. When did you first realize that that's a good thing to have?
Colin Sidoti:
I mean, we realized it early on. I think it was very much in the 2019 pitch deck of this two act thing of you get user identity first and then the thing I just said about you don't just charge, you charge users, you don't just email, you email users. That was literally a slide in the 2019 deck that we used with South Park Commons. So it's really always been there. I think we've seen auth as just a bigger opportunity if you execute it right from the start, and I think that's what made us think we could do an actual venture business here.
Turner Novak:
I think you mentioned one time, you were talking to John Colson at Stripe.
Colin Sidoti:
Yes.
Turner Novak:
And what's the story there?
Colin Sidoti:
So first of all, I met Stripe 2011. I don't think they had launched yet. I was in beta and got introduced to John. And I was getting dinner with him. I tell myself that he wasn't recruiting me, he probably wasn't, but it would be a really big mistake if he was, financially, for me.
Turner Novak:
So he was just a friendly, just come get dinner with this guy?
Colin Sidoti:
So this gem of a human, his name's Darragh Buckley. He was the first employee at Stripe. And I think they're mates from Ireland is the story. And I had gotten introduced to him and he showed me Stripe for the first time. And then John was at my college to do just a guest lecture thing. And I got dinner with him. And I was still super early, and we were talking about just payment space. And pretty sure he was giving me this spiel about there's only X on E-comm so far, and every year, it's going to get more and more, and it's endlessly big, and we're going to take over all payments.
And I had this gut reaction of like, "Yeah, but you're never going to get Amazon." And he was like, "Why not?" Just pure dead pan, completely serious, "Why not?" And that's the one thing that sticks with me from that entire dinner. And I think for one, they went and they did it. It took them 10 years, but Amazon now uses Stripe. I think they first got in there by way of acquisition and so on, but they're now a very big user of Stripe. And to just see how quickly things can compound, I think it is just very inspiring. And yeah, I feel like I've adopted a lot of that in Clerk. And we get the same kind of comments, like this XYZ massive enterprise isn't going to switch to Clerk. And it's just like, maybe not today, but...
Turner Novak:
Five years, 10 years, it's a long time.
Colin Sidoti:
Yeah.
Turner Novak:
There's a lot of new features you can add. A lot can change over that time.
Colin Sidoti:
And I think to me, the way technology has evolved, or at least developer tools have evolved, is they're now more trusted to be experts. And so, if you look at even just the evolution of Stripe, they famously started, seven lines of code for the charges API. Nowadays, most people use checkout. And if you think of how much more you're seeding, you're seeding the whole UI to Stripe. And the idea is that Stripe can build a better payments UI than I can.
And Clerk is very much the same way. We think we could build a better sign up, sign in, and then all of these areas that we expand into. And we expect that over time, more enterprises are going to actively seek that out. It's going to be less of this, "Oh, I want to outsource auth, but we do this weird thing in our application. Can you support it?" It'll be more like, "I want to switch to Clerk for auth, and I want to switch to the Clerk way." And that's really what we're after and how we approach it.
Turner Novak:
I think you've mentioned to me before in the past that you are very opinionated on, we don't build any custom features or changes to people. It's just we are opinionated, and you will either use us or you won't. Why do you do that? Because in theory, you might lose some customers because of that.
Colin Sidoti:
Yeah. I mean, so we definitely do lose customers. I think it's a little bit of just speed. Right now, what's more transformational for Clerk's business? Is it getting a big auth enterprise, or is it $100 million in payment volume through the billing product? We have limited resources, and so right now, we'd rather put those resources to something that expands everyone's perception of Clerk, right? I'm still pitching it as auth, but if we want to be unshackled by that $6.5 billion ceiling of Auth0, which is what they sold for, and we think we can go much bigger.
Turner Novak:
So what is the products we consist of today?
Colin Sidoti:
So it's primarily user management, so sign up, sign in, user profile.
Turner Novak:
So this is, if I'm creating a product, I need a way to create accounts for people, I need a way for them to log in?
Colin Sidoti:
Yep.
Turner Novak:
Okay.
Colin Sidoti:
Then there's the B2B SaaS side. We call it the B2B SaaS suite. But it's organization management. So B2B customer comes in, they tell you what organization they're a part of, and then they invite their teams. They might set up SAML for them. So that's B2B SaaS suite. Oh, they set roles and permissions and things like that. And then we have, I would say, half a product right now on administration. And so, we have a feature called user impersonation. And so, we have a lot of companies' support teams. When they get a ticket in and customer is saying they're seeing something, they can go sign in as that user and see it themselves. And so, that's our third product. But yeah, all of that, I think people still see as authentication. And so, billing is really going to be the first that's like, "Oh, wow. This is a bigger entity."
Turner Novak:
How else are you thinking then about potential other things you can do? You just talked about we want to prove that we're more than just auth. What else could this consist of?
Colin Sidoti:
I really like CRM. And I think the idea is if you go to a big software company that has account execs, and salespeople, and a deal desk, it's normally this operation that runs in HubSpot, Salesforce. And there's this big disconnect between the software they're using and the actual source of truth of customer data, which is the application.
Turner Novak:
So, how is that?
Colin Sidoti:
It's like you'll have a sales team, they'll sell a thing, and then they'll hand it off to a deal desk, and then the deal desk will go work with the engineering team to go turn on that customer with all the right settings.
Turner Novak:
Based on what they bought?
Colin Sidoti:
Based on what they bought. And so, there's this very... It's always built in-house. It's usually hacky, different degrees of sophistication depending on the company. But if someone's selling bespoke plans, which almost everyone does in B2B SaaS world, the process of turning things on is actually really hard. And so I really like CRM, because it's not so much about the crud of CRM, of taking the notes from the call today.
It's more about after the thing is sold, since Clerk does authentication and we're doing more and more of authorization with both who are you in your organization, what role do you have, and what permissions come with it. But then we're also entering it more with billing, where, what plan are you on and what things come with that plan? We'll get to this world of the sales team able to work in Clerk tooling and actually enable those features directly for that customer in a very clean UI, and it's all kind of connected.
I think there's just so much manual in that today, and it's all hidden because these are enterprise deals, they're massive contracts, you can pay to have people manually doing it. But we think that there's just an opportunity to actually give a singular interface in a way that CRMs haven't been able to do it. And then, of course, we'll also have to do the classic CRM functionality. But we see that as maybe slightly easier. Naively. I'm sure I'm going to learn that lesson three years from now, like, "Oh, this is a horrible idea to get into this."
Turner Novak:
Slapped in the face. So I guess, to say it back to make sure I get it, so currently today, when a deal closes, there's a lot of custom work that just needs to get done to get something live, versus what you think you'll be able to do with Clerk is literally I'm the salesperson, I close the deal, and I just say, "This company has these features," and I click the button, and it's just live in the product for the customer already?
Colin Sidoti:
Yeah.
Turner Novak:
That's pretty crazy.
Colin Sidoti:
There's no enablement phase, is sometimes what salespeople will call it. Like, "Oh, yeah. I just sent this over to the deal desk to get enabled."
Turner Novak:
Interesting. Okay.
Colin Sidoti:
And it's just like they throw these words at you and you're just like, "Can you just turn it on, please?" And so, that's what we want to enable. Yeah.
Turner Novak:
Okay. For authentication, it's one of those things that sounds extremely boring. Extremely.
Colin Sidoti:
It is.
Turner Novak:
I'm impressed people that are still listening to this.
Colin Sidoti:
No one should want to do it themselves. Absolutely boring.
Turner Novak:
The people listening to this podcast, they're like, "Oh, man. They must really be interested in authentication." So what does good and bad authentication just look like from your perspective, of somebody who's really in the weeds with it?
Colin Sidoti:
I think the main thing you need to remember with auth is that it's changing all the time. And so, just in our lifetimes, I'd say started with just username, password, and then we added email. And when we added email, we had to verify email, and we had to do a forgot password. And then sign in with Google came out, and sign in with Facebook came out, and then Facebook had that Cambridge Analytica thing, and sign in with Facebook is off, right?
Turner Novak:
I forgot about that. Yeah.
Colin Sidoti:
I'm pretty sure that's how it happened. I don't know.
Turner Novak:
That's crazy actually.
Colin Sidoti:
Yeah. But there's just been all of these changes. And for a while, it was like we're all going to have wallets, and we're all going to have passkeys. And passkeys, I think they're still growing in adoption, but people are a little more tepid about passkey is going to be the change. And so, it's always changing. And even just in Clerk's lifetime now, we've had crypto, we've had passkeys. And today, it's agent auth. How are we going to let agents sign in for humans?
And so, it is boring. I think the actual question of what is best right now, the Clerk defaults are you have sign in with email and password, and then we have sign in with Google. If you go to sign in with email, after you sign in with Google, and you haven't set a password, then we'll send you an email with a six digit code so you can sign in that way. And yeah, for password managers, you still want to have passwords there. Most people are using Google, so we're at like 65% now. And so, that's really like, you have to have it or you're just killing your conversion for no reason.
Turner Novak:
Because people just expect they'll just use their Gmail account to sign up?
Colin Sidoti:
Yep. Yep. That's 65%. When we started, it was like 45% for our first six months of growth, and over time, it's just taken more and more. Yeah, I think... Then there's 2FA, and there's the YubiKeys, and there's the TOTP. There's just all these elements. You can't just take a password. Before you take the password, you have to check Have I Been Pwned to see if it's been breached before. There's just this endless array of things. I wouldn't even say it's hard. I think boring is good. You just want to follow the best practice. It's undifferentiated. And so it's kind of right to just outsource.
Turner Novak:
Yeah, it sounds like the perfect category, or product opportunity, or market to make a company like Clerk around, because it's one of those things no one wants to do themselves, it's really boring. No one on the team is going to sign up of, "I'll spend three months doing this," but you kind of need to do it. And it's always changing. So it's better to just have it outsourced to expert shop that has 100 engineers. I don't know, maybe you're not 100 people yet, but maybe one day.
Colin Sidoti:
Yeah.
Turner Novak:
Massive team that's just constantly giving you best in class.
Colin Sidoti:
I think that's the pitch. And a lot of people, when they do still do it in-house, which is normally with an open source tool, they'll typically cut some corner. And I think what they don't realize is that corner is cutting a reasonable amount of conversion, and ultimately Clerk is faster to set up than open source tools today. And I think that was a thing that we had to accomplish to make Clerk grow.
But to do it, it's like, well, we have to have user storage. We have to have an email provider baked in. We have to have basically demo credentials for sign in with Google. We have to have Have I Been Pwned hooked up for you. There's all these things that we have to do to be able to make it truly faster than what you would do yourself. And so, yeah, I think you end up with both a faster setup getting off going, and just a more complete, polished, higher converting setup out of the box.
Turner Novak:
Yeah. So it sounds like a reason to use a product like Clerk is you have an opinionated way of doing something that the customer can choose whether your way is the best way to do it, or they could use an open source tool that may be different way of doing it. But your pitch with Clerk is basically, we spent a lot of time thinking about this. We just think this is the right way to do it.
Colin Sidoti:
It's really similar to Stripe Checkout, where there's so... If you look at the last couple of years of Stripe announcements, it feels so focused on, oh, and Stripe Checkout now converts 5% and 11% better. I think when you get into that mindset of not just functionality, but am I really myself going to think about truly streamlining this as much as possible? No. Clerk does have a huge team that's just thinking about it all the time. Why push that friction on my customers when this is here and it's affordable? We go along, we try really hard to make sure that everyone can use Clerk.
Turner Novak:
Then how did you initially come up with the idea and start doing this?
Colin Sidoti:
Yeah. I don't get the privilege of calling myself a serial entrepreneur because they all failed. That seems to be a thing. You're not a second-time founder until you have one that partially works.
Turner Novak:
But you were constantly just trying things?
Colin Sidoti:
I was constantly trying things. I graduated college like 2014, but even while I was in college, I was doing startups. Then we started Clerk 2019, so there was that whole time I was doing startups and just surviving.
Turner Novak:
They weren't even going good enough to say that we had built a startup. It was like, "We're trying things."
Colin Sidoti:
No. No. They had gone good enough. One of them... Yeah. No. They were going good enough that I was able to sustain myself without ever picking up a job.
Turner Novak:
Yeah. That's fair then. You could say [inaudible 00:26:35] serial. You're an entrepreneur. You're constantly trying to find ideas.
Colin Sidoti:
I would think, but the number of fundraising conversations I go into where it's like, "You're a first-time founder." Okay. I'll take it. Whatever
Turner Novak:
Those are fundraising conversations with VCs that will... The thing with VCs, it'll be someone's got this business that's doing 500 million in revenue, or it's like a CPG brand that does a 100 million in revenue. It's like, "It's a lifestyle business."
Colin Sidoti:
There you go.
Turner Novak:
It's like, "Dude, that guy's business does more in revenue than... Profit than revenue of all your entire portfolio."
Colin Sidoti:
The bar is high.
Turner Novak:
You call it a lifestyle business, but it's like it's not easy.
Colin Sidoti:
The bar is high. But anyway, suffice to say I was building a lot of things. Every time you build something you need to do auth, and so I had this... The other thing about the past starts, I had this intuition that I'm not good at the business stuff, and so I'm going to be the technical founder. I know how to code. I'll find good business people, and they'll handle that.
Turner Novak:
They'll do business.
Colin Sidoti:
They'll handle that side, right?
Turner Novak:
Yeah.
Colin Sidoti:
The last one fizzled out, and I wanted to do something else. I was like, "You know what? This time I'm going to do the business side," and all I know is developers, so I picked a problem that I hated. I had this feeling of Stripe is easy to set up and ALT ZERO is hard to set up. I can just do auth easier. I got lucky with Braden, my brother/co-founder. He was looking at new jobs at the time, and he was at an agency, a we build apps agency. He had spun up tons of apps where he also faced this problem of just the zero to one, all the stuff you need to set up.
It resonated with him, and we just built a proof of concept. This is January 2019, and spent a couple of months on it, two months on it. Then we did a little fundraising thing here in San Francisco, went to South Park Commons, and they gave us... We were like a guinea pig for the founder fellowship, so we were a worst deal. I don't know. They give so much more money now. But yeah, and then we were the first... It was us and two other companies at the time.
Turner Novak:
Cool.
Colin Sidoti:
Now they've turned it into more of a real program.
Turner Novak:
Back up a little bit. What is it like to work with your brother as your co-founder? I think it's a question from Reed at CRV.
Colin Sidoti:
Reed is CRV.
Turner Novak:
He's got some other ones that's strategically inserted in here.
Colin Sidoti:
I'm excited. What I like to say is we have 30 years of experience arguing with each other and coming out on the other end. I think early on that was actually probably really helpful because there were a lot of fierce debates, and it's good [inaudible 00:29:56] especially while you're finding PMF, be able to just fiercely debate and know at the end of it you're still going to be working on this thing together. More recently, I think the most helpful thing is the trust that's just baked in because as the company grows and there's just so much to do, we found that there's a lot less time for us to actually talk to each other.
This is actually a mistake new employees make. They'll come in thinking the two brothers are on the same wavelength 100% of the time. Really it's like, "No, he's got his part. I got my part, and it just goes. Then we sync up and periodically to make sure we're still on the same page." But having that just blind trust that he's not going to mess it up, and he has that trust in me, it's fantastic. There's never a question there.
Turner Novak:
What was the living situation like when everything started?
Colin Sidoti:
The living situation? Yes. He lived in Denver. I lived in Boston. We get into this South Park Commons thing that they're doing. It doesn't even have a name yet.
Turner Novak:
In San Francisco?
Colin Sidoti:
In San Francisco. We had just flown in for two weeks. We were staying on whatever hotel Priceline's express deals where they don't tell you what hotel you're going to get, they just tell you the price. We did that. Stayed in the cheapest hotel. We were out here for two weeks, do a ton of pitches. We get into South Park Commons. I fly to Denver, and then we drive his car out and we're staying... Basically my friend from college, she had just bought a house and she had an empty basement, and so we're in the basement paying $400 a month, which is a great deal in San Francisco.
Turner Novak:
Yeah. Splitting it two ways. Right?
Colin Sidoti:
Yeah. We said, "We're going to be here for eight weeks," which is what South Park Commons said is an eight-week program. It's going to be roughly like Y Combinator.
Turner Novak:
Eight weeks, you'll find PMF. Off to the races.
Colin Sidoti:
Off to the races you'll go. You'll raise the seed. It'll be great. We get there, and we're paying 400 bucks a month. Six weeks in, we don't feel like we're leaving South Park Commons anytime soon. She's picking up on it, and she's like, "I think I'm going to start increasing your rent 100 bucks a month." Anyway, so we ended up staying there for a full year, all the way through COVID. We're in South Park Commons every day, basically open to close. Yeah. Kelly Klon, she's not an investor, but she's on our cap table.
Turner Novak:
Does that mean you just gave her some shares?
Colin Sidoti:
No. She did invest. That's actually another funny story. I asked her for an introduction to someone that is an investor, she does a lot of angel investments. She's like... I should just say the name. It was Maia Bittner. She's on Twitter, and she's at Chime now. I was like, "Clerk has this FinTech angle. We're going to do billing." She does FinTech angel investments. Kelly and Maia are friends. I know that because I met Maia at some party she threw, and we were looking for angel investors.
I'm like, "Hey, Kelly, could you intro me to Maia?" She's like, "Why? I was like, "I'm looking for investors." She's like, "I want to invest. If I invested in all of my friends' Series A companies, I'd be rich right now." She never even made the intro. Maia doesn't know this story, so this will be a fun... She swooped up the last $25,000 we had in that round. But yeah, it's crazy to think all of the little things that people did, like Dara I mentioned, he introduced us to Anurag, so he introduced me to John Carlson back in 2011. Then in 2019, he introduced me to Anurag, who was in South Park Commons, who introduced us to South Park Commons. There's so many little things. Kelly kept us going for an extra three months just with the low rent.
Turner Novak:
Is there a way that you have opened up more serendipity there? Like leveraged getting introduced to people? How should I think about that if I'm early in this and I'm like, "I want to be introduced to angel investors and people that will help me"?
Colin Sidoti:
I just try to say yes to everything with friends at least. Yeah. I don't know. If a friend is doing something, I always try to go, and I always end up meeting more people. It's really easy to be too tired to do it, but I just always try to go and it's ended up... I just met some amazing people over the years. Honestly, I think it's just I always try to say yes. If someone invited me, I should try to go.
Turner Novak:
Some guy invites you on his podcast, say yes.
Colin Sidoti:
There you go.
Turner Novak:
Yeah.
Colin Sidoti:
Here I am.
Turner Novak:
Yeah. You mentioned that this period dragged out. You lived in the basement for a year.
Colin Sidoti:
Yeah.
Turner Novak:
What was it like trying to get people to start using the product? How did that go?
Colin Sidoti:
This is why we stayed there for a year. It was amazing. South Park Commons, they have this program of they have once a month new people start, and they have a whole little onboarding thing. It's not just... South Park Commons has a community in addition to the fund. The community, it's all just these technologists that are normally like, "I was an early employee at X, Y, Z thing. It grew, and I'm trying to decide what I'm going to do next. I'm going to go hang out at South Park Commons." Those people are amazing demo tester people. Every [inaudible 00:36:08] come in, we'd be charging through the door after their onboarding, and be like, "Hey, can you try out this thing?"
Turner Novak:
It's unofficial onboarding is also a [inaudible 00:36:18] click.
Colin Sidoti:
Yeah. It was fantastic. Basically we'd do it, and every time they'd hate it, but we'd get some nugget of like, "Okay. This is what we have to do for the next batch of people. We want this improvement done." At the end of the year, first of all, we were running out of money, but we started as a RubyGem, and by the end of the year we had honed in on, okay, React has something here that has more legs than we ever saw on this other thing. We know that we needed the UIs, and so a lot of the plan had started to formulate.
Turner Novak:
Then what was the thing that really switched with people? Was there a certain feature or something that got you there or decision that you made?
Colin Sidoti:
I think it was a little bit of the persona.
Turner Novak:
Just nailing the customer and the user persona?
Colin Sidoti:
I think React developers are front-end developers, and they're used to like, "I need to build a sign-in page. I have to go ask my backend team to stand up these endpoints for me so that I can do it." The way they see Clerk is more like Clerk is their backend team unless... They don't care about the implementation details beyond that. We get tripped up a lot with the average Ruby developer or Python developer or so on, because they'd watch the demo and they'd be like, "That was really cool. That was really fast." Then they start overthinking like, "Where is my data though? I never connected this to a database," and it sounds scarier than it is. We have APIs to access all this stuff and so on. But with the React audience, they were just like, "Wow, you're just helping me move a lot faster. This is great."
Turner Novak:
Basically you just got... Would you say part of it is just getting narrower and focusing?
Colin Sidoti:
Yeah. Yeah. I think that is really a big thread because we started very agnostic. We thought that that was the right thing to do.
Turner Novak:
Yeah. Because everyone could use it.
Colin Sidoti:
Everyone wants an agnostic solution, and the more we honed in on, okay, not just all developers, but React developers really like this. Then we did another phase not before the first seed round, but later on of not just React, let's go all in on Next.js and really try to have an amazing SDK for that one framework. Now we have all of the different React frameworks and other front-end frameworks and so on.
Turner Novak:
Yes. You never really gave up on the big vision, but you really just figured out, okay, this is one language and this one type of developer. Then you added another, and can... If you're using Python, can you use it now?
Colin Sidoti:
You can.
Turner Novak:
Okay. Well, here you go. Yeah.
Colin Sidoti:
Yeah.
Turner Novak:
Start super narrow, and then go a little bit more broad.
Colin Sidoti:
I think it was almost more like a change in who we sold to with the React emphasis because so many React apps have a Python backend or Ruby backend and so on, but it was still easier for us to get in the door through the React developer.
Turner Novak:
You mentioned a couple of times the fundraising, and that was initially how we connected on this was posted a clip from the podcast from Villi talking about category ventures, and we were talking about seed extensions.
Colin Sidoti:
Yes.
Turner Novak:
His initial thinking was you're most likely to get a seed extension from a smaller fund. You end up raising a seed extension from k16z.
Colin Sidoti:
Yes.
Turner Novak:
Literally the biggest fund out there really at the end of the day. You hit on a little bit of the fundraising with South Park. What's been the fundraising journey? Because it has not been the most straightforward and you read a blog post about how this goes-
Colin Sidoti:
How much time do we have?
Turner Novak:
Yeah. I'm curious, just some different things you've made work on the fundraising side?
Colin Sidoti:
Yeah. It's been a slog most steps of the way. I think... We started with South Park Commons, and-
Turner Novak:
What was their deal that they did?
Colin Sidoti:
I think it was like 200,000 for 5% was the initial deal we were on.
Turner Novak:
It was like it's this fellowship. We'll coach you. You'll learn how to make a company, build a product. You'll go and raise the seed round?
Colin Sidoti:
Exactly.
Turner Novak:
Okay.
Colin Sidoti:
We'll do it in eight short weeks.
Turner Novak:
It sounds like a great pitch [inaudible 00:40:57]-
Colin Sidoti:
My wife, by the way, was still in Boston. She loves to talk about how eight weeks turned into eight months.
Turner Novak:
Oh, man.
Colin Sidoti:
"Then he asked me to move out here." All vaguely happened. She moved out for COVID. Anyway, yeah, so we did that. Yeah. I was saying at the end of the year we had switched from RubyGem to React and the product was better. It was more well-defined. At South Park Commons, we got lucky that we pitched to Aditya. Aditya was like, "I worked on the counts at PHP at Facebook. I absolutely hated it. I would love for someone to take over this whole thing." That was it, and super early. We had a proof of concept, and he was like, "Okay. This is enough. Let's try this out."
Turner Novak:
He was a prime user of the product, and you just happen to pitch somebody who was down a fair way, would've been a customer.
Colin Sidoti:
Exactly.
Turner Novak:
Totally got the pain point.
Colin Sidoti:
Which it turns out it's very hard to know before you pitch someone if... I had no idea Aditya had worked on accounts at PHP at Facebook.
Turner Novak:
You might've tailored the pitch differently if you knew that he had encountered the problem.
Colin Sidoti:
We should come back to that.
Turner Novak:
Okay.
Colin Sidoti:
I don't think I would have.
Turner Novak:
Okay.
Colin Sidoti:
I think it was tailored to him, and it just wasn't tailored to anyone else. That's why South Park Commons did it and no one else did. But so a year later we're doing the first seed, and we figured out this React thing, but we're not launched.
Turner Novak:
Were people using it?
Colin Sidoti:
No.
Turner Novak:
Okay. That's scary as an investor, it's like, "Spent a year. No one's using it yet."
Colin Sidoti:
Very reasonably so, very scary. We might've had one friend's company from New Jersey that we built the whole app for him and we put our app in it [inaudible 00:42:58] in it too. Right?
Turner Novak:
Okay. That's a hack to get customers. Build their entire product.
Colin Sidoti:
My brother worked at an app agency before this. What else do you good for now?
Turner Novak:
You had less than six months of runway at this point, right?
Colin Sidoti:
Yeah. It was more like two months of runway.
Turner Novak:
Okay.
Colin Sidoti:
But it's just the two of us.
Turner Novak:
You could have in theory had indefinite because you could have just-
Colin Sidoti:
In a sense.
Turner Novak:
Yeah.
Colin Sidoti:
We're pitching them, and basically this round was... We probably talked to 40 people. It's not resonating with anyone. It was like four weeks of this, it's just getting nowhere, looking to do anything we can. We applied to YC. We didn't get into YC.
Turner Novak:
What was the hack? I know you had this trick that it made it start to work.
Colin Sidoti:
Yeah. Ruchi, the other SPC partner besides Titia, came out with this nugget of like, "You've mentioned during this that some associates liked you, but the partners, they couldn't get it over the line with the partner."
Turner Novak:
Yeah.
Colin Sidoti:
It's like, "Why don't you email all those associates and say, 'Hey, is there one fund that you'd recommend we talk to?'" She was very adamant about one fund. Don't ask for any fund, just like, "What is the one best fund you think we should talk to that might do this?" An associate from Index came back and said, "I know this fund S28 that is looking for something like this. I'll make an intro to Vic." Made the intro, we show up, and it was basically the same situation as SPC in the sense that they're engineers. They understand what we're talking about. They have a bunch of portfolio companies that are experiencing the auth problem. They all hate it, and it's a little undefined. They were thinking about incubating something, but they were like, "Hey, you showed up on our lap. We might as well do [inaudible 00:45:03]-
Turner Novak:
[inaudible 00:45:03] invest. Yeah.
Colin Sidoti:
Yeah. Like, "You want to keep working on it. Let's go." That was the first seed, we still haven't launched.
Turner Novak:
Yeah. You did end up getting a pretty strategic angel that helped you out that came in.
Colin Sidoti:
It wasn't in that round. It was in... S28 ended up doing a follow-on round.
Turner Novak:
Okay. I think you officially launched a couple of months later, right?
Colin Sidoti:
Yes. A couple of months to a year.
Turner Novak:
Okay.
Colin Sidoti:
It was a long journey.
Turner Novak:
Hey, that's totally fair.
Colin Sidoti:
At this point, the proof of concept was resonating with people. If you were an engineer, you saw it and you're like, "That's cool. That'll be great."
Turner Novak:
Was there a-
Colin Sidoti:
It was totally hacked together. It wasn't production ready, so we spent a ton of time making it production ready [inaudible 00:45:46]-
Turner Novak:
Okay. I was going to ask, is there a reason that you didn't launch? It was like you were just trying to make the product good enough?
Colin Sidoti:
I think there's two sides of the product. One is like, "Do we get the DX?" Right? Then the other is are we actually comfortable launching this thing? Because we are still a security reliability company. Your auth can't go down.
Turner Novak:
Probably you can generate no revenue. People can't use your product either.
Colin Sidoti:
Yeah. In this phase of just looking for what is the right product, we had no regard for making it production ready. Really, the way we were framing that for a seed round was we have this [inaudible 00:46:25] concept. It's resonating with people. We have to now make it work and launch the thing and rebuild. It was a big rebuild of the backend, and it's like you almost don't even want to call it rebuilt because the backend was just non-existent.
Turner Novak:
It wasn't rebuild. It was a build.
Colin Sidoti:
It was mocked together. Yeah.
Turner Novak:
Yeah.
Colin Sidoti:
We built the thing, and then we launched it Feb '21. That launch on Hacker News went really well.
Turner Novak:
People were... Your audience is developers on Hacker News. It's people like, "I hate this problem. I hate creating this stuff."
Colin Sidoti:
Yeah. It took off. The headline was, "All of user management, not just authentication." That resonated with people. The components resonated with people, and we got a nice little spike of signups. Then it did the classic straight into the valley.
Turner Novak:
But you took advantage of the spike, right?
Colin Sidoti:
Yeah. We took advantage of the spike. S28 saw the spike, and I guess they've probably done this somewhat strategically. Initially they made a smaller bet, and then they doubled down on their bet and gave us what they thought was enough capital to get us to the A. Yes. In that round, they actually said, "We're not the most networked investor in the world. We think we should pull in John Komkov from Fathom, and he's going to help us get the A done whenever time is." I'm like-
Turner Novak:
Whatever.
Colin Sidoti:
... "I don't care at all." Right? Fundraising has not been our prowess. Meanwhile we have competitors that are literally raising a $100 million with seemingly no effort. I was like, "What is going on?" Anyway, someone's throwing money at us. We'll take the deal. You want us to bring in Komkov? Absolutely no problem. I actually really enjoyed the call with Komkov, but there was no way I was saying no. Right?
Turner Novak:
Yeah. This is probably the easiest raise you'd had at this point-
Colin Sidoti:
[inaudible 00:48:43]-
Turner Novak:
... where people were just like... Probably biggest dollar amount with the least friction, I'm assuming.
Colin Sidoti:
Exactly. Yeah. It was preempted, and so we didn't know it was coming. They gave us two weeks to decide on it.
Turner Novak:
Yeah. That's incredible. You go from just convincing somebody to say yes to like, "We want to give you more. Here you go."
Colin Sidoti:
Absolutely.
Turner Novak:
"Just sign this thing, and we'll send you a couple million bucks."
Colin Sidoti:
We did that, and... Yeah. Then the company progressed from this spike on Hacker News launch day into this valley of we're getting you signups every week. We're able to talk to those customers and see their friction points and so on, but there's still issues with the product. It's not just going.
Turner Novak:
What decisions and product changes did you make?
Colin Sidoti:
I'd say if I were to characterize the full product period between when we launched and when it really started growing, it was this transition from React Diagnostic to Next.js specific in a sense. The extra tuning we did to make it really great for Next.js I think pulled... We're talking 12 minutes down to six minutes in terms of integration time. It's a big deal.
Turner Novak:
Why is that a big deal?
Colin Sidoti:
It's half the time.
Turner Novak:
Okay, fair. Did you see conversion rates go up when you were-
Colin Sidoti:
That's generally the only trick we have in the book, is like, "Look at your onboarding, how many steps is it, and how can you get rid of a step?" If I were to characterize all of Clerk's lifetime, that's what we've been doing, is just, "How do we take steps away?" Yeah. I should say, we pitched... We're just naming everyone. We pitched Sequoia early on in the seed, and I actually really liked the feedback they gave. This was the S28 round, that was really hard, so they were one of the 40. They came back and said, "Stripe took this many week process and turned it into hours, and Twilio did the same thing. Many week process, turned it into hours. We just don't know if taking hours," which is what Auth was that, "Taking it down to minutes, if people are really going to care." That was what they relayed when they passed, and we didn't know either. I really appreciated that feedback, because it was like, "Well, that's a real... You thought about it. That's real feedback."
Turner Novak:
I mean, a lot of people just don't even give you feedback and you don't hear from them ever again.
Colin Sidoti:
Yeah.
Turner Novak:
Yeah.
Colin Sidoti:
We've always had this belief that, if we just take the onboarding steps and we just try to remove steps one by one, eventually, we'll get faster than open source. We'll just be the fastest way to set things up, and developers are just ruthless about, "How efficient can I be?" Yeah, I think that process for react to for Next.js just made the onboarding that much easier, and that's ultimately where things started to pull.
Turner Novak:
Making it easier to use the product, reducing the friction, speeding onboarding was the thing that really started to start to tick up?
Colin Sidoti:
Yeah.
Turner Novak:
Yeah, I think you mentioned...
Colin Sidoti:
Unfortunately, it didn't happen before we needed to raise a gap.
Turner Novak:
Okay. This is probably about a year process of continuing to just-
Colin Sidoti:
Yeah, so we launched FAB21 and then we were down to six months runway in... It was fall of '22.
Turner Novak:
You were going to raise your third extension, or you thought you were going to raise a series A.
Colin Sidoti:
We were going to raise an A.
Turner Novak:
Right, because he was working, sort of, right?
Colin Sidoti:
We knew that wasn't going to be an easy round, because I always think of Paul Graham's Started Equals Growth essay, and they're like, "It's a good YC company if they're hitting 7% growth week over week," and we hadn't done that at the time when we were down this six months of runway. We knew it wasn't going great, but I think what was interesting was that we had customers that loved us. We were only growing 3% week over week, we were under 100 grand of ARR, but we were launched. We go to do this other round, and honestly... I guess, playing it out, we had done that really bad seed and it was four weeks followed by pure desperation. This time, we were like, "We know what we're doing, so we're going to schedule it all in two weeks," and so a week ahead of time, we email all the VCs, "We want to meet in these two weeks."
Turner Novak:
That's what all the blog posts will tell you to do when they give you advice.
Colin Sidoti:
Exactly.
Turner Novak:
Box it all in.
Colin Sidoti:
We do that and most fit neatly into these two weeks, and Comcov, same guy that we strategically brought in, he was like, "I know a guy at Andreessen. I'll get that meeting set up," and they set it up for three weeks. We're just like, "All right." At this point, Andreessen had already passed too in a prior round. It's Andreessen, how are you going to get Andreessens? Like nothing's working, really, 3% growth. No way it-
Turner Novak:
They're not Going to [inaudible 00:54:46] but it's good to just catch up with that one.
Colin Sidoti:
They're off the table anyway, but we should go talk. Yeah.
Turner Novak:
Yeah.
Colin Sidoti:
Anyway, we do these two weeks and miserable. No one's there, we get into the third week, I think we have one or two follow-up meetings, but not feeling very good about it, and we go into this Andreessen meeting that Friday morning, and the best way to describe it is, for me as a founder at least, I had done so many demos of Clerk. Customers come in, they want to see a demo, "Okay, I'll do the demo with you." I know exactly when people react and when they get excited, I know what step and so on. I'm like, "For this pitch, we're going to do the same thing. We're just going to demo Clerk and see if they like it." VC meeting after VC meeting, there's no reaction. All the hit points, there's nothing there, and I do it with Andreessen and Martin stops me at the first hit point. He's like, "Holy shit." It's just like-
Turner Novak:
You're like, "Wow, this is great."
Colin Sidoti:
Well, "Yeah, thank you."
Turner Novak:
Yeah.
Colin Sidoti:
The meeting keeps going on and, at some point in that meeting, I say, "The component is the new API," and he latches onto that. He's like, "That's brilliant. React is taking off, yada, yada." He ends up tweeting it out after the meeting.
Turner Novak:
Yeah, you sent me that tweet. I actually liked it, I'm wondering, "I'm wondering if it'll show up in his notifications that I liked this tweet from two years ago."
Colin Sidoti:
At this point, you're just doubting everything. So that was my first indication like, "Maybe he's actually going to do it."
Turner Novak:
Yeah, that's got to be incredible feedback of you got excited about the one thing that actually most customers get excited about, and then he tweeted about it.
Colin Sidoti:
Not a big part of the pitch.
Turner Novak:
Yeah.
Colin Sidoti:
They end up working through the weekend, I do the partner pitch on Monday, and we get the verbal "Yes." I don't know how deep we're diving here.
Turner Novak:
We can go as deep as you want. Based on everything you've said, that probably felt incredible at that point of, "Holy shit-"
Colin Sidoti:
It did.
Turner Novak:
After three years, it sounds like, or maybe it's more than that, of going through this, somebody finally gets it.
Colin Sidoti:
Yeah, and I think [inaudible 00:57:21] and S28 got it, but it wasn't launched yet. To see an investor at a huge fund get it-
Turner Novak:
With not super exciting spreadsheet math there yet, right?
Colin Sidoti:
Yeah.
Turner Novak:
Only 3% weekly growth.
Colin Sidoti:
Yeah.
Turner Novak:
You're not going to die, but you're not going to usually get A16Z to invest at that point.
Colin Sidoti:
Exactly. We get to a verbal yes, but they're just like, "This isn't an A, you don't even have 100 grand in ARR."
Turner Novak:
I actually have a portfolio company that I'm... A very similar setup, where A16Z did an extension with... It wasn't an A, but they were excited, and been going well since then. Actually, probably pretty similar path.
Colin Sidoti:
Amazing.
Turner Novak:
It started to do well afterwards.
Colin Sidoti:
Yeah, it's hard for me to be upset at big funds for not doing extensions as a result.
Turner Novak:
It was technically a down-round, right?
Colin Sidoti:
Yeah.
Turner Novak:
How did this play out?
Colin Sidoti:
This is the nitty-gritty of it.
Turner Novak:
You hear about a Series C or Series D down round, but not even an A yet down round, that's harder for a lot of people to swallow. How did you do this? How did you pull that off?
Colin Sidoti:
Oh, man. We get the verbal yes, meaning Jason wants to invest, but then they're like, "You've done two seeds already, this cap table probably..." They said, "We don't think this cap table is set up for you to turn this into a big business businesses, so at the end of this round, we want the cap table to still look like a regular seed company, so that when you go to do an A..." That was the other thing I said, "It's not A, it needs to be a C." When you go do an A, you're not underwater already in terms of dilution and so on. It was not a down round for employees and founders for common stock. The way they executed it was... It's called a re-capitalization. They basically redraw the whole cap table, all of our existing investors got basically over-diluted, and then the founders in common stock got under-diluted.
Turner Novak:
Okay.
Colin Sidoti:
That's how we pulled it off. It's way easier said than done, right? Existing investors don't like the extra dilution.
Turner Novak:
Yeah. What did you say or how did you present it?
Colin Sidoti:
I mean, so at this point, the investor that has to make the call on whether or not to do it is S28, because the way our docs are written up, it's not like you need approval from every check, you need approval from the majority of the preferred, and in this case, it was all S28. I think maybe we needed SPC's approval too, but S28 was clearly the main driver here, and it was not... It's not fun. As a founder, you're, first of all, immensely thankful for all of the investment you've gotten that's taken you to this point of getting Andreessen funding and, really, any funding. Anything that lets you continue, you're just immensely thankful for anything that's gotten you there. To have to pick up the phone and be like, "They want to do this thing," it's not particularly fun.
I don't think it was received particularly unexpectedly. It's not like I'm getting yelled at on the phone, but it's just like, "Well, this sucks," and we all kind of have to acknowledge that. It ended up being... This is why it's funny, Comcov was part of this, that introduced us to A16Z. Comcov ended up mediating, in a sense, the down round for S28 while bringing in Andreessen. Yeah, I mean, I think Comcov is... If you ever have a chance to meet him, absolutely do. He's the most level-headed rational person ever. This was the last meeting, but we did our two weeks meetings, everyone said, no, there is nothing else on the table. Maybe we could take this and parlay it into finding money from someone else, but-
Turner Novak:
A16Z wanted to invest.
Colin Sidoti:
Yeah. Do you really want to do that or do you want to take the money from the person who has conviction? It's just very rational, "Yes, this is the best thing, but it still sucks."
Turner Novak:
He was part of the down round too. He negotiated his own down round-
Colin Sidoti:
Yeah, really negotiated his own down round. That sucked, but we signed it and that was exciting.
Turner Novak:
Yeah.
Colin Sidoti:
I know everyone talks about founder rollercoasters. This week was the most insane week, and there was something going on. I think S28 was in the Maldives or something, something ridiculous.
Turner Novak:
[inaudible 01:02:40] vacation.
Colin Sidoti:
He's Indian and it's like his...
Turner Novak:
Okay, slightly, because it's in the Indian Ocean, right?
Colin Sidoti:
It wasn't pure... Classic VC, "I'm going to go to the Maldives."
Turner Novak:
At least it was next to-
Colin Sidoti:
Also, he's not the Maldives guy. He's going to watch this and be like, "What?" No, he's not at all. It might've been right after he got married. It was totally-
Turner Novak:
Yeah, slightly more fair. I'll give you more credit.
Colin Sidoti:
We're dealing with a massive time shift at the same time, and it was just nightmarish, but exciting at the same time. That was a week of founderdom for you.
Turner Novak:
Well, I know there was something that you mentioned, you changed the pitch based on feedback from S28. I think it was after you launched on Hacker News, the way you talked about the company to investors, you completely changed, which I think maybe that helped with A16Z, but what was that lesson that you learned?
Colin Sidoti:
We actually ended up with a rule in fundraising, "That Colin's not allowed to talk about billing in pitch calls." This was a rule from Brayden, because he's like, "Everything sounds so normal and sane, like Auth0, people don't like Auth0, there's room for a new entrant here, and then you go and you talk about how you're going to take over billing and you just sound completely unhinged. You're not allowed to talk about billing anymore." That happened in the round with S28, that first slog of a round. Looking back now, I think that was the wrong move. I think it felt right, it felt like the easier thing to pitch, but when we went and we did the Andreessen round, we were no holds barred.
We're doing the pitch, "This is the thing. We're starting Auth, we have the second act into all these things." The same way we did it with it for SPC. I think that behavior of, "I'm going to try to do what the VCs want," instead of, "I have a conviction around how this business is going to work," and, "I'm going to pitch this in a way that deliberately scares away the people that don't get it," it's a big switch flick there, but I think it pays off. I think Martin, in the Andreessen pitch, he was excited about all. He wasn't just excited about Auth, he was excited about this platform of components that help in more verticals than just off.
Ultimately, you're just better off having people on your board that are aligned with the full thing, because otherwise, you end up hating your board. You don't want that. You don't want that back pressure, you want people that are egging you on to go do more and more and more. I learned that from S28 as part of the extension round, because basically, it was preempted. I wasn't thinking about them giving us more money at all, it wasn't on my radar of things that they would ever do, and so at this point, I know what I had pitched them, but whenever I'm do a check-in calls with them, I'm always talking about like, "One day, we're going to do this thing with billing. It's going to be amazing." When they did the extension, he called me up and he said, "I want you to know I'm doing this not because I think Auth is going to be a massive business, I'm doing this because you won't shut up about billing." It was such an empowering moment of, "First of all, thank you for seeing that, right? I love how you see that, but also-"
Turner Novak:
That's a vision that you saw.
Colin Sidoti:
Yeah. Also, it makes me so much more excited to talk to him and strategize with him about how we're going to do that one day. And that just makes for a much more enjoyable working relationship for me at least. Now, every investor knows, and we talk in board meetings about this, "This is what we're doing for the grand plan." I don't know, it helps. While it's very tempting to do the thing that you think will get them to write the check, you're probably better off pitching it the way you actually want to see it go, and then just play a numbers game. I can't promise that Andreessen is going to be the one number that happens to like it. That's just a weird thing that happened for Clerk, but it doesn't matter who the check comes from. What really matters is the partner alignment. When founders ask me for fundraising advice, that's consistently the thing I say, and I think the people who get multiple checks, they constantly get caught up on this, "What's the best brand?" And, "What's the valuation?" And so on. In the early stages, none of this matters.
Who's the partner that gets it the most? That's the one you want to work with. I think this is part of the Vili thing too, of like, "The multi-stage funds don't write seat extensions, and the smaller funds do." Who cares? It's just partner alignment, that's the thing that matters most.
Turner Novak:
Yeah.
Colin Sidoti:
The partner that's truly aligned with you is going to be the one that grows the pie with you in the way you want to grow the pie.
Turner Novak:
I mean, maybe a pushback on the, "Doesn't matter about valuation, dilution, brand," whatever. Let's say you have an investor that no one's heard of before and you take a really low valuation, bad deal. You saw too much of the company, A16Z's point about, "We need to fix this cap table a little bit." You want to think about those things too, though, don't you? Shouldn't you care about those?
Colin Sidoti:
I honestly don't know.
Turner Novak:
It sounds like maybe the underlying truth is survive.
Colin Sidoti:
Yeah.
Turner Novak:
That's really what matters more than anything else.
Colin Sidoti:
I think there's this element of... I guess there's probably some bounds here. A partner that's aligned needs to still be playing realistic, right?
Turner Novak:
Yeah.
Colin Sidoti:
I think the 20% rounds at anywhere from 15 to 50 million valuation is realistic, easily. What do I see? What's the YC default seed these days?
Turner Novak:
It's like a million at 20 or 25, yeah. Sometimes it's more, sometimes it's less. If it's 15 or less, the general thinking is YC doesn't really know how to think about this company, there's no interest. Just talk to people and a low valuation possible, get the deal done.
Colin Sidoti:
There's these rough standards that exist, and you think of YC at the high end, where people are... No matter what, these early rounds, they tend to be 20%.
Turner Novak:
Yeah.
Colin Sidoti:
15, 20%, 25% sometimes. You need to make sure that they're playing within those bounds, but beyond that, I just really think far and away partner alignment, it's the single most important thing and everything else is second, third, fourth, fifth.
Turner Novak:
Yeah. I mean, and part of it too is just the business model of those funds, is they need to try to get 15 to 20% ownership. That's why it's the rule.
Colin Sidoti:
Yeah.
Turner Novak:
It's really like the VC is almost putting it on the founders. If you can only sell 10% of the company, that's great. If you can retain more ownership, that's good.
Colin Sidoti:
Yeah. On the founder side, my advice is don't twist yourself into knots. Which partner do you like the best?
Turner Novak:
Yeah.
Colin Sidoti:
Then just grow the thing.
Turner Novak:
Yeah. I know we just spent half an hour talking about how much fundraising sucked, but it sounds like it started to get better. You've launched, you're launching, been more mature.
Colin Sidoti:
Yeah.
Turner Novak:
I think you mentioned you actually hit the YC 7% of wheat growth shortly after.
Colin Sidoti:
Yeah. We caught it in January. Technically, another round happened before we caught it.
Turner Novak:
Then you were proper series A couple months later, right?
Colin Sidoti:
No, it's weirder than that. In recent, did the round in, I want to say... It was September it closed, or August, something like that. At this point, we're still at 3% growth, and then I get an email from Karan Mahanju at Madrona, newly at Madrona. My first instinct is like, "What is Madrona doing emailing me? They're a Pacific Northwest Fund." For the audience who probably doesn't know this, there's this fund called Madrona, they were based in Seattle, and their thing forever was, "We do only Pacific Northwest Investments."
Turner Novak:
Yeah.
Colin Sidoti:
Apparently, they had just hired this guy in San Francisco, Karan, to start investing out of San Francisco. I had no idea. In our 40 pitch slog, for all I know, Karan would've done it and scheduled in those first two weeks, and so on, but I didn't even reach out. He emails us before the end recent round is announced and says... He was on Auth0's board, so that's a big part of this. He basically talked to his Auth0 confidants and said, "Which one's going to win next?" Apparently, they unanimously said Clerk.
Turner Novak:
Wow.
Colin Sidoti:
He was super jazzed, and this was a company still growing lightly, but again, we have this element of, "People who get it, get it," and so if you're really looking at Clerk and its customers at this point, the customers are all happy, there's just not a lot of them yet.
Turner Novak:
Yeah, probably product people can really tell, a customer of the product who's seen the landscape, and, "This is the best one, that one's going to win."
Colin Sidoti:
Yeah. Yeah, Karan comes in and he does an A November. Still hadn't grown yet, so we managed after this absolutely brutal round of the recap, two months later, this extra check walks in. It's the same situation as the S28 extension of like, "Yeah, of course we'll take the money."
Turner Novak:
Well, I mean, did you need to fundraise, though? Why did you take the money?
Colin Sidoti:
Definitely not, but money has never been easy for Clerk to come by, so-
Turner Novak:
You were just like, "Someone wants to give us money, we should take it, because we don't know when this will happen again"?
Colin Sidoti:
Yes. Yeah, there's also this element of, "We have this grand plan. We know we don't have enough money to get through the grand plan, we don't have enough money to even build billing, the first step of the grand plan, so we'll definitely take the extra capital and, yeah, so, that was a couple of meetings, didn't talk to anyone else, just open and shut, let's do it. And then comes January, and that was the first time we finally broke this 7% week-over-week thing.
Turner Novak:
How did that feel?
Colin Sidoti:
That was amazing. That was actually ... Fundraising is exciting, but this is just 10 times more exciting.
Turner Novak:
Because people were finally using it, and you was like, when you go from 3% a week, to four to five, you're growing faster every week.
Colin Sidoti:
Yeah.
Turner Novak:
As you get bigger, you're growing faster.
Colin Sidoti:
And that was just, you start to feel it, and people start to feel it internally. And up until that point, you can imagine just the degree of doubt about, "Is this decision right? Is that decision right?" And so on.
Turner Novak:
Yeah.
Colin Sidoti:
But once the market really starts pulling it, it's like, "Okay, we've got something going right." That was January '23. Luckily, had the A in the bank. It's also the month we launched, or we announced, the Andreessen round. Even though the A was already done,. We just didn't tell anyone.
Turner Novak:
And then, I think you had an interesting situation with the next time you raised money.
Colin Sidoti:
Yeah.
Turner Novak:
You kind of told me, just how you negotiated that. So, this is with Reed at CRV, for the Series B.
Colin Sidoti:
Reed at Series B.
So yeah, Reed had, I think, always liked, at least us, as founders, like Brandon and I. My take, at least, he didn't mind the grand pitch. He was just, "It's just the market's not taking it yet. How am I going to do a round right now?"
Basically, once we started hitting those 7% numbers, and I think what helped Reed a lot was what I said earlier, "A lot of what felt like it ended up driving it was this shift from React to Next JS." So he invested in Rizell, as well and was able to verify with Rizell people that are like, "Okay, it's actually doing something cool."
So that started in January. I think it was May or June. I get a call from Reed that's like, "Hey, this seems to be working now. I always liked you guys. Why don't we do it?"
Yeah, so, the way that one went was, he gave us terms. At this point, we had just done the A, in quick succession with the seed. And so I called up, my team said, "Hey, we just got this term sheet, CRV." He's like, "What's the price?"
And I forget what it was, but he was like, "That's too low. We're going to beat it. And then, you should just go shop it around." He's like, "If you shop it around, and no one else does it, then we'll do it, we're happy to," but I think you could beat it, basically, and so ...
Turner Novak:
He gave you some ammo to work with.
Colin Sidoti:
Exactly, yeah.
Turner Novak:
But it sounds like, it wasn't, it didn't quite land right away, right?
Colin Sidoti:
What do you mean, didn't land?
Turner Novak:
Well, so then, how did you convince CRV to come in at the higher price, yeah?
Colin Sidoti:
I convinced CRC, yeah. I mean, so I told him he got beat, and this is funny, right?
Turner Novak:
He got beat? Okay.
Colin Sidoti:
Because here I am, just ranting about how it's all about partner and we really liked Reed, too. So we were excited to have his term sheet.
But yeah, there was a lot of this back pressure, saying, "You have to get the price up from ..." It was really both Madrona and Andreessen, but Andreessen actually gave us this extra term sheet to go do it.
So I went out for beers with Reed, and yeah, I kind of imagine it was scheduled for an hour, but we were there for three and a half hours, just at the bar. And we don't even get a table at this restaurant.
We're just literally at the bar, just talking you through, and there's not really anything to discuss. It's just, "I want you to hit this number." And he's just, "don't want to hit that number. I don't think I can hit that number." It's like, "All right, let's get another beer."
We just did this for hours. And at some point, several beers in, I'm just, "I need more ammunition here." And so, Guillermo from Rizell had gotten in, I forget which round. I think it was one of the S-28 rounds, because S-28 also invested in Rizell.
And so, I'm DM'ing Guillermo, "Hey, I'm at a bar with Reed, I need to get his price up. Can you help me?" He then texts Reed while I'm sitting next to him. It was like a whole comedy of a night. He was just buying food.
I don't know. We just hashed it out. I think that was a very fun night for me, I mean, not just because the next day, he calls me up, and he is like, "Fine, let's just do it. I like you guys. This looks really stupid on paper, but we're going to do it."
And it did, right? Revenue at this point? We're probably the only Series B company.
Turner Novak:
It was 2023.
Colin Sidoti:
It was 300 grand of ARRs. It's still embarrassingly low.
Turner Novak:
Yeah.
Colin Sidoti:
It's so early in the curve, and you're right, it's 2023. So Clerk, if you look at the timing of our investments, Zerp was basically, it was mid-21 to mid-22. So that second S-28 extension we did, maybe Zerp was starting then, but I don't know, we had this, we had an extension, and we were just going to take it, right? We didn't even think we totally missed Zerp.
Our competitors, multiple competitors raised over $50 million, and one over $100 million dollars, basically, as far as we can tell, with the same revenue. But we missed the whole thing. So you're right, 2023, to be doing a Series B at 300 grand of ARR, not totally normal, but for whatever reason, Reed's the same, I guess, and did it. But now we're making a bunch of money, so it's okay, yeah.
Turner Novak:
So another question from Reid. He specifically asked me to say, "What is your thoughts on investors that are in the arena? And then, investors that are watching from their mansion on the couch, on TV?"
Colin Sidoti:
Did he mention the Maltese in there?
Turner Novak:
No, he didn't.
Colin Sidoti:
It's a funny question, because he clearly has someone in mind.
Turner Novak:
Yeah, I'm not sure.
Colin Sidoti:
I think we've only had success with investors that really get Clark, and I think a lot of the partner alignment point comes down to, do they understand the business in a real material way, and your ambition, in a real material way?
Turner Novak:
Yeah.
Colin Sidoti:
For all I know, he's talking about Martin. And Martin is the one in a mansion, somewhere on his couch, but he probably has a laptop there, and he's playing around with Clark in 11 labs, and all these things.
Turner Novak:
That's from what I've heard about Martin, he's a lot of doing demos and trying it.
Colin Sidoti:
I think he's had just an incredible track record. And I've had other investors ask me, "What do you think Andreessen does?"
And my answer is, "I literally think he sits and codes all day, with all the new tools, and he picks the ones that he likes the most. I think that's it, I think that's the alpha.
Turner Novak:
Yeah.
Colin Sidoti:
And it's not just Martin, his whole team, Yoko and Jen, they're just incredible at staying on top of all the technologies. And yeah, I as infrared investors, I think that's their whole shtick.
Turner Novak:
Yeah, you might think that the A-16-C is in the mansion watching on TV, but yeah, to your point, it's like they might actually be the ones in the arena of using the products.
Colin Sidoti:
Yeah, I agree.
Turner Novak:
Yeah. And to the company I mentioned earlier, was like a similar setup. It was a very similar story, where just, good product, not a lot of traction, starting to look better, they invested, because I was the best tool. So it seems like this seems to be, I don't-
Colin Sidoti:
I see I'm outing everyone during this. You won't tell me this company name. I wonder who it is.
Turner Novak:
It's called Ingest. Have you met Tony?
Colin Sidoti:
I know Tony, yeah. Of course, I know Tony.
Turner Novak:
Yeah. I don't know if you have a similar opinion on it, but it seems like a good product.
Colin Sidoti:
Yeah, it's a fantastic product.
Yeah.
Turner Novak:
Yeah, their onboarding experience, we copied at Clark.
Oh, interesting.
Colin Sidoti:
They did this thing before us of, "You can use Ingest, before you have an ingest account."
Turner Novak:
I didn't know they did that.
Colin Sidoti:
Yeah, and they did it from the start.
Turner Novak:
Okay.
Colin Sidoti:
And getting to that after you've launched is actually quite hard. So it was a big six-month build for us to get there.
Turner Novak:
Oh, wow.
Colin Sidoti:
It did help us. We got an extra bit of acceleration immediately after launching it.
Turner Novak:
Oh, cool.
Colin Sidoti:
So, big fan of Tony, big fan of Ingest.
Turner Novak:
Nice. Yeah, I don't use the product. I just met him when he was at Uniform Teeth, and he just seemed like, I'm like, "Oh, this is an interesting idea," I guess, in theory, but just seemed like a great founder, "I'll give you money," helped him raise the first round, I think, introduced him to a floor who led the pre-seed.
Colin Sidoti:
It's a lot like Clerk, too, in the sense that they layer so much elegance on top of what is really thorny, in terms of durability of cues, and workflows, and things.
Turner Novak:
Yeah. Seems like a similar, just unsexy stuff, like you don't really want to do, and if someone else solves it for you, that's great.
Colin Sidoti:
"Let me just pull this off the shelf."
Turner Novak:
Yeah. So curious, then, talking about just AI, I mean, I feel like it's a podcast, we're two tech bros, we have to talk about AI.
Colin Sidoti:
Yeah. Of course.
Turner Novak:
But I feel like, we can have a very opinionated, how has it changed authentication? Or how do you think it's going to change authentication?
Colin Sidoti:
Yeah. Well, there's two angles that are coming to mind right now, but I might think of a third, as I go through this. But the first is, id the stack changing, or not? And I think Next.js has been kind of the stack du jour for so long, but it's been Next.js with a human operating it.
And I think a lot of the agents are using Next.js still, but the human's not there. And then, some agents are actually trying different stacks entirely. DQo, Clark needs to be on her toes, from this perspective of, who's going to be the one installing Clerk now, and are they good at doing it?
I think that exercise is actually very similar to what we did in '21, '22 of just, how do we pull friction out for this user we're observing? It's just like, now, it's not a human, it's an agent. So we look at the mistakes they make, and we try to peel away those mistakes.
But then, there's the other side of just, how is authentication itself changing? And I think, "Yeah, I'll split this into two different ways that it feels plausible, or going to happen."
First is just agents signing in on behalf of a human, and this is what you see. MCP has a lot of buzz around it right now. It's this idea of, can you give an agent a partial set of permissions to act on behalf of a real human in an application? Or a full set of permissions, if you want to be a little more YOLO about it, I guess.
Turner Novak:
I don't know how else to frame that. Just do whatever you need to get done.
Colin Sidoti:
Yeah, I think there's a lot of identity people, myself included. We really don't want that to happen. We think that we want the application builders to have more checks and balances on it, and we want the humans to be actually participating in granting certain privileges, or not.
So that's what MCP is enabling. There's this other pillar, that I think is really interesting, that Dharmesh is, like agent.ai. Have you seen that?
Turner Novak:
Yeah, I haven't used it, but it's the thing ... He's the HubSpot founder-
Colin Sidoti:
Yeah.
Turner Novak:
... CTO, builds a lot of products.
Colin Sidoti:
Yeah.
Turner Novak:
He did this, he just started building things, and talking about them, AI products. He was trying, basically.
Colin Sidoti:
What I love about agents.ai is, it's framed as, "Hire an agent to do a thing for you," on some website. And when you hire an agent, that agent isn't necessarily impersonating you. They'll just do any task, and they'll do it as the agent. So there's this question of, do websites need to start thinking about just an agent entity operating independently, instead of an agent entity operating on behalf of a human?
And I think the simplest way I have this framed in my head is, say you're, I don't know, a task board, project management software, and you have your team there, and you can kind of imagine, someone has their tasks at the end of the week, to clean up dead tasks and reorganize things, pull things out of backlog, and so on.
You can kind of imagine an agent doing that. And that agent doesn't need to be on behalf of a human. It can just be the agent doing it
Turner Novak:
As part of the software, as part of just-
Colin Sidoti:
Yeah.
Turner Novak:
You don't need to have somebody say, "Click a button, and do this." It's just, it notices that it needs to be done, and it happens.
Colin Sidoti:
It almost, it gets attributed to the agent. You see the thing, it's all audited, but the agent did it, and that's not a human, but the agent did it, and you can reverse it, and so on.
So it's like a subtle nuance on it, but you can actually imagine software selling a seat to an agent. And that agent has its thing that it does, and maybe it's an add-on agent.
Who knows how it's going to happen? But I really think agent.ai really pushes me down that track of, "Oh, this would be an interesting way for agents to evolve." So those I'D says, I guess are the three ways I'm most thinking about AI right now.
Turner Novak:
Are you seeing any interesting data in Clerk usage, with how agents interact with Clerk?
Colin Sidoti:
Yeah, they all try to steal free AI credits.
Turner Novak:
Steal Clerk credits, to use the product cheaper, or ...
Colin Sidoti:
Not Clerk credits. Our customer's credits.
Turner Novak:
Really? Okay.
Colin Sidoti:
Yeah. So we have a ton of GenAI tools, and they have these free trials.
Turner Novak:
Oh, yeah.
Colin Sidoti:
And you get your 10 credits on your credits, whatever.
Turner Novak:
It is.
Colin Sidoti:
And the sophistication of the bots that try to sign up for these things, and use the credits en masse, has just gone way up.
Turner Novak:
So the agents will be creating new accounts, to get more free credits?
Colin Sidoti:
Yes, yeah.
Turner Novak:
Wow, that's crazy.
Colin Sidoti:
Do the human operators tell them to do that? Or you think the agents are becoming self-aware?
Turner Novak:
I think there's human operators, still, yeah.
Colin Sidoti:
Okay, okay. AGI not achieved?
Turner Novak:
Yes, sadly. It's honestly been a massive thread at Clerk. We have 10% of our team just focused on understanding when this is automation against your website, versus when it's not. Because most of our customers actually want to block abuse behavior.
Colin Sidoti:
Yeah.
Turner Novak:
I think they also want to be able to identify non-abuse happy agents, and let them in. But so far, the biggest thread for us has actually been blocking abuse that's been more easily enabled since agents, and browser base, and things like this.
Yeah, wow. That's crazy.
Colin Sidoti:
It's been fun.
Turner Novak:
So one thing I want to ask you, one more thing. You mentioned to me, you always try to have fun.
Colin Sidoti:
Yup.
Turner Novak:
I don't know if that's always what I hear from founders, but that's actually probably pretty important. Just why is that so important to you?
Colin Sidoti:
I think it's definitely too easily lost, right? I think VC is a very serious business, with very grand ambitions, and a lot of money at stake. And with the number of zeros attached, that it's really hard to even grok.
And so, yeah, I think for me, though, I can't lose sight of that, or I'll go crazy. So, the silly nights at the bar, drinking tons of beer with the VC, trying to convince him to raise his price?
Turner Novak:
Yeah.
Colin Sidoti:
But even just talking to customers, and tweaking demos in fun ways, and so much of what Clark does, is just try to bring a smile to people's face as they're building, and on a part of the stack that's just traditionally such a slog. And yeah, I don't know.
I've talked to so many founders that they have this huge success story, like, sell single digit billions, high, a hundred digit, hundred millions, whatever, and they're just exhausted at the end. So one of my big things as a founder is whenever I meet someone who's not that, I just probe it, "What did you do? How did you make it work?"
And Patrick Carlson sticks out to me, Dharmesh and Brian, at HubSpot, stick out to me. There's just these legends that have had such a long run, and there's always this mention of just, you got to love the work, and find a way to make it enjoyable.
So it's just something I keep in mind, and try to keep in the team's mind as we go forward, because to me, Clark isn't something with a finish line. We're building this, and it's just going to keep going. We're going to hang going off, we're going to hang CRM off. We're just going to keep doing more things.
And so, we have to craft this company in a way, where, if something is getting us down, we have to find a way to get rid of it and move forward. And so, yeah, it's just part of it, and I think longevity in this career just depends on it.
Turner Novak:
Hm. Yeah, that's fair. I actually have one more question. You mentioned there are quite a few people in the space that are kind of building off, like a lot of people, it'll be a feature of something else they do, like it's part of Google Cloud or whatever, My Offer, or something.
Colin Sidoti:
Yeah.
Turner Novak:
How have you thought about differentiating the product, as auth-only?
Colin Sidoti:
Mostly DX. Yeah, our work is really, really fantastically easy to use. And after you do the very few steps to get Clerk running, you look at it, and you're just like, "Oh wow, that's also really, really complete, in a way that I never would have imagined it would be complete."
You open the user profile, and it's just like, there's more there than you expect. You go in the dashboard, and from an administrative perspective, there's more there than you'd expect. So a lot of it is just, DX to delight people, but then-
Turner Novak:
Developer experience, just-
Colin Sidoti:
When the thing is actually, people forget that DX isn't just, "Make it work as delightfully as possible,"but the part that ends up working needs to also just knock people's socks off. So I think we've just done that really well.
Turner Novak:
Just make a product that's just better, and people choose it.
Colin Sidoti:
A little bit, yeah.
Turner Novak:
Yeah.
Colin Sidoti:
Build it and they will come, right? That'll be the ...
Turner Novak:
Yeah, you can't say that, but I guess, as an outside observer, I could say, it seems like that's what you're doing, so ...
Colin Sidoti:
A bit, yeah. I mean, we are 100%, a product-led everything.
Turner Novak:
Yeah.
Colin Sidoti:
Yeah, there's a lot of taste that comes with it, and I think that's probably a big factor for us. But yeah, I don't know. I look at other products, and it's like, ours is better. I think it's better.
Turner Novak:
Yeah. I guess, if you're still listening at this point in the conversation, you're thinking about trying it, you're thinking about, "I want to join an awesome mission, check out clerk," it sounds like, that's-
Colin Sidoti:
Definitely. Yeah, both of those things. Please try Clerk, and if this is exciting, and I really think it is, and you'd want to work on this grander vision, please do apply. I think it's clerk.com/careers.
Turner Novak:
And you tweet a lot, too.
Colin Sidoti:
I do, yes.
Turner Novak:
You're pretty active on Twitter?
Colin Sidoti:
Yes.
Turner Novak:
Do people follow you? Is that a good way to stay-
Colin Sidoti:
I'm tweets by, my name is a little dated at this point.
Turner Novak:
It's called X. X's posts by Colin.
Colin Sidoti:
Yeah, we're going to stick with Tweets by Colin, it's a-
Turner Novak:
It's a throwback.
Colin Sidoti:
It's enshrined. Yeah.
Turner Novak:
Cool. Well, there's a lot of fun. Thanks for doing it.
Colin Sidoti:
Thank you. Thanks so much for having me.
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