Brett (00:00) I'm Brett Glanson. I was one of the very early employees at Calendly. started in 2014 and stayed with them for seven years. Company size of three people to over 500. Valuation of under a million dollars to about three billion when I left. Just a

very rapidly growing company. I think that's what you wanted to talk about was the experience of coming through that.

Michael (00:33) Yeah, for sure. I think this is super unique now looking back about the opportunity that you got and what it was like and it is valuable for other people. Set the context for us. What were you doing just before Calendly and how did you hear about that opportunity?

Brett (00:48) I was working for a company called Blink Media that did like ad campaigns on Facebook. ⁓ It combined two things I really didn't enjoy, which was Facebook and advertising. ⁓ Didn't really feel like I was contributing to the world in a positive way. So I was looking for other things. I was interested in Bitcoin and a recruiter had reached out about a Bitpay position.

⁓ that, didn't work out. We were, were in, ⁓ the Atlanta tech village. ⁓ I'm sorry. I was in midtown at the time, but, ⁓ in Atlanta tech village was, ⁓ bit pay and they were kind of starting out and getting bigger. They were one of the earlier payment processor, ⁓ solutions for, for Bitcoin transactions. And so I was really interested in working with them. This was 20. This was also.

earlier, I think in the year 2014. so Bitcoin was proven to be pretty big deal, but like still extremely, I it still feels a little early in a lot of ways. But so I was excited about that. That didn't work out, but the same recruiter had connections with Calendly because both were in the Atlanta Tech Village kind of co-working sort of incubation sort of.

⁓ programs. And ⁓ it looked ⁓ appealing. It looked like a potentially a CTO role, which at the time was something that was really appealing to me. ⁓ And ⁓ yeah, I went through many rounds of interviews and eventually started ⁓ with Calendly as lead engineer, but I was the only technical hire. So

It was kind of a funny title because it took a couple of years for there to be other, at least internal engineers that I was leading.

Michael (02:50) What else attracted you to Calendly? Calendly seems so different than Bitpay, right?

Brett (02:57) ⁓ in both cases, I saw huge potential, huge, huge upside potential. ⁓ Calendly was much faster realized it was in hindsight, it was definitely the better bet. But, ⁓ I had, I had created, ⁓ several kind of failed startups, ⁓ before this time. And I found, and I, and I.

worked with other, I'd worked in several startups as an employee. I ⁓ was just kind of in startup space and some of the big issues that I always saw over and over ⁓ were two main things. One was ⁓ cost to acquire new customers. Usually that ends up being investment in sales, investment in marketing, stuff like that. You have things like

⁓ example I like to give on, well, actually this is more applicable to the other thing. The other thing is critical mass. There's a lot of, there's a lot of solutions or product solutions that don't really solve anything until you get enough people over to them. Imagine you're going to try to create a competitor to YouTube. It wouldn't matter how good it is if no one's there. ⁓ know, the creators would want to go there. None of the viewers would want to go there. ⁓ so those are two.

Just themes that I saw over and over. It's like, this is great, but you're just going to burn through all your cash just trying to get customers on board. Or this is great. Or this would be great once you got to this place. Calendly didn't have either of those problems. It did not have the critical mass problem. It was many, many years later when we started to create sort of network effect features that benefited from two people already both being in Calendly.

for the first five years that I was there, you could be the only user uncountably. And ⁓ it wouldn't matter. It would work just as well as if they had a huge user base. So I saw that while interviewing and I thought that was exciting. But the other thing was that just the way the app works, it's naturally inherently viral. It's people are in many cases paying you.

to advertise for you because they get a link, they share that in every way they can think of because there's, like you could also frame this as like your interests are aligned, the business interests are aligned with the interests of the users. The users want to get this other person to come to Calendly, choose a time and have a good experience and have a good meeting. And ⁓ we wanted that too. When that person goes through, there's...

there was a certain percentage likelihood that they would sign up for their own account because they'd see how easy it was. And ⁓ they'd want that for their own endeavors. So, yeah, we didn't really have a marketing team. didn't really have a sales team for many years. Again, like these are, this was a, ⁓ it was a beautiful, beautiful business model and ⁓ hard to replicate. ⁓ I think it was half brilliance and half luck.

⁓ on Tope's part that it kind of fell together that way. Tope being the CEO of Calendly.

Michael (06:28) Got it. So when you joined, ended up joining, what was the product? What was the state of the product when you joined?

Brett (06:34) ⁓ About three or four months prior, they started charging users for ⁓ premium features. think at the time it was mostly just being able to have more than three event types enabled at a time. ⁓ Pretty good delineator between a casual user and a power user is if you have many different types of meetings that you want active at the same time. ⁓ So I think they

Uh, just this was, this was before I came on, but I think they just, anyone who had more than that, I think they just got disabled and you know, the excess got disabled until they had signed up. And at the time when I joined, I want to say. I could figure this out because our user IDs were sequential. Uh, so if I dug into the API, I could figure out my original user ID and figure out how many users there were before me. But I think it was about 60,000 users.