The Exchanges

Q do you, I mean, for those people listening right now going, okay, we're going to do user conference this year. We're going to try it. Okay. I'm listening to Jason talk on Nathan's show in 2015 with his first thing. You know, we want to go from 500 to 1500. I mean, was it more ad spend in the second year? Was it just word of mouth? Was it not?

A Second year, we didn't even, I didn't even have a list like we have today, like you and I have today. It was just word of mouth. It was just blog posts and tweets. And, um, it wouldn't work today. We could not, I mean, we'll have over 10,000 this year. If I just waited on word of mouth, it'd probably be smaller than it was in 2016. Cause the world has changed. Right. But back then there was no content in sass and cloud. You, you're an innovator too. Like people, there was such a, no one had ever heard a VP of sales talk, like, or a CEO talk. Now you can fire up YouTube and there's a thousand talks from Aaron Levy, who I love. He's done saster six times.

AI assessment note: “It was just word of mouth. It was just blog posts and tweets.”

Q And what was the breakdown in terms of revenue between ticket sales and sponsors?

A You know, the beauty was the first two years, um, I took, I outsourced it. Here was another life learning. I outsourced it to our good friend, Max Altshuler, who runs Sales Hacker and just stepped down as VP of marketing and outreach. And he had run a sales event. And I said, Max, you can keep all the money. Like, I don't want the money. You know how to do this crazy thing. You do it. You keep all the money and just, just help me. I'll do the speakers and the content and the marketing. And so I didn't even know this actually the second year we ended up doing 3.6 million the second year. And I can, and the breakdown was about 50 50. Um, but everything broke and we lost actually lost money that year, even though we went from, from 400 K in revenue on 200 K in cost. We lost money in the next year on 3.6 because it just got too big too quickly.

AI assessment note: “and the breakdown was about 50 50”

Q Well, and what did you tell me before for this? I mean, you said if,, I mean, I guess I'll just ask the question. If you knew what goes into putting on an event like Sastra annual come out here, September, 1314, 15th, right Yeah.? Would you, would you do it again?

A No. And look, it is a, it is, um, You know, it is a work of passion at this point. We know what we're doing. We're passionate about it. These are the things you want to do in life once you've been doing things for a while is find things that you're, even if they're quirky, that you're passionate about, right? Because it keeps you going. But no, no one told me there's no book. I mean, at, at, at this scale, you know, the overall enterprise is like twenty five million. You start to reach this weird air where there's not a lot of comps and people to talk about. And so after the second year, the first year was, 800 people during the day, one day event, 1400 organized in 90 days. You get that. Cause you're doing that now. It was great.

AI assessment note: “No. And look, it is a, it is, um, You know, it is a work of passion”

Q Super rare. Yeah. Super rare. Hey, last, last set of questions here. Um, as we wrap, I mean, well, actually first preface, if you weren't doing Sastr today, what would Jason Lemkin be doing?

A Well, I don't know. I probably would be investing better. I think about this a lot. I've made some pretty good investments. Um, I'm about 10 X lifetime. Um, first investment pipe drive first venture investment acquired for 1.5 1,000,000,002nd. They're worth almost three billion front top desk, ten billion. I had a pretty good run and I have some, some pretty good ones now. Um, it seemed very easy for a while to do everything when the world was smaller. Um, and I, If you're curious, I think sometimes should, in a different world, if I didn't care about this community so much, right, should I have just built a billion dollar venture capital firm for SaaS folks? It would have been actually very easy to do knowing what I knew now, right?

AI assessment note: “I probably would be investing better.”

Q What was the leader, the leader lesson you're going to give?

A Um, the question, the, the, the mistake I made was, can you do, can you, can you be, if, if you like to be a macro manager and hands-off, I certainly do. I like to hire great people and I've made some big mistakes at SAS or I never did before and get out of their way. The question is, can you do that if you don't know how the function works? So I didn't know how event production worked. I didn't know how AV worked. I didn't know how any of these things worked. And when you hire someone to do a role, but you don't know how it works yourself. It's like hiring a CTO. If you've never coded, like it's super risky.

AI assessment note: “can you do that if you don't know how the function works?”

Q the MNA strategy for Saster wasn't, how do we go find and buy another Jason? Cause you're never going to find another Jason, but it's more about how do we go buy something that enables Jason to take 20 minutes of his time, one interview keynote on stage and cut it up seven more different ways. Would you go by that process or a business running that sort of process?

A I think it's a smart thing. I think that, I think that, uh, yes. And that's what, you know, dating ourselves or dating myself, that's what it's so long ago, but that's what they tried to do with TechCrunch, right? Is to keep it back in the day, only some folks listening to this will know, but when they bought TechCrunch, they wanted a bit of Michael Arrington, right? AOL, but AOL is a big company. It didn't really work, but keep doing the disrupt when disrupt was a big deal. Keep doing these guest posts. This, you know, TechCrunch used to be Michael Arrington. Now most people don't even know who Michael Arrington is. But yeah, he was a superpower in Silicon Valley when it was small.

AI assessment note: “I think it's a smart thing. I think that, I think that, uh, yes.”

Q So what is that? When you say event production, what is, what does Montgomery do?

A Well, we've got seven stages, 250 speakers, uh, hundreds and hundreds of, they've got to set it up. It takes a week and a half to set it up. They got to manage all, like, there's different folks that do other things. They've got to manage all the AV recordings, food. They got to feed 10,000 people. We have Duke Dumont doing a party. We've got to deal with their, their agent at Creative Artists or whoever it is. We have, like, other DJs. We have three art cars coming from Burning Man, and then they don't want to come anymore because we're too close to Burning Man. And like there's hundreds and hundreds of vendors to deal with. And when we've hired mediocre people, you know what they all, I'll give you one last lesson on this. If you're doing stuff at scale, the meat, this is my first experience, life experience with this, the mediocre people in events, you can't on a software release, you can slip the date, right? We're supposed to have this feature in founder path. It's supposed to come out next week. Nathan really wants it, but if it's not ready, you can slip it a week. Can't you? Or even a month, right? Events. You can't slip the date. You can't slip the date. So what happens is the mediocre people, it's not just, they don't get it done. It's bad enough. They lie. They all lie. Nathan, they lie.

AI assessment note: “seven stages, 250 speakers... They got to manage all the AV recordings, food.”

Q Well, how do you do it? So is it a one-on, is it a mail merge? You send it through HubSpot mail merge one-on-one, it looks like it comes from you?

A I should, I should send it from me. We have historically, um, I've tried to be very careful about what comes from my name. I'm a little bit, I tried right or wrong. I mean, for chatting, I've tried to be a little less commercial than you are. Um, um, I think you, your, your community and brand allows you to be more commercial. You're very direct. You're very direct. Mine is, you know, what comes first, second, third, fourth, and fifth community. Okay. Then maybe comes a sponsor and maybe comes a revenue, but it's, Put the community first for now, 10 years, eight years of events, 10 years of content, and then going long there will pay off. So I, I've allowed the team to send one or two emails a year from me.

AI assessment note: “I've allowed the team to send one or two emails a year from me.”