A keynote-style talk by Jason M. Lemkin recounting his journey from founder to community builder and the evolution of the SaaStr community. He describes origins (Quora backdoor), early growth, launching SaaStr Annual, challenges scaling the event, impacts of COVID-19 (≈$10M loss), and plans to reboot an outdoor, vaccinated/tested SaaStr Annual in 2021–2022 with ambitions to become the central annual gathering for the SaaS industry.
Chapters
I was a founder myself. So two startups, the last one a company called Echo Sign that Adobe acquired. Real story of the community is when I was a VP at Adobe, there are social media limitations. So if you want to tweet or if you want to blog or do any of these things, it needs to go through PR. And so I decided like a 30 day turnaround for tweet was a little long. So I got out the HR policy and it was prescriptive and it said what you couldn't do, but it hadn't been updated in years. So it said you can't bebo, you can't MySpace, you can't Geocities, you can't do all these things. But it didn't say you couldn't. So it turned out Today we crossed 1300 SaaS. Answers on Quora. This Quora loophole was kind of the backdoor that created this community. We all thought we had this, that this kind of hit a Plateau around 2011, 2012. We had figured out all the applications were built marketing automation, sales automation. It was kind of stable times where we would grow like this. Instead, boom. With about 60 days notice. We did the first Saster annual in 2015 and over 1600 people came. I should have realized that meant we had initial traction and scale to have Aaron Levy and Stuart Butterfield and other leaders come when there had never been a community event for sas. Today it's all a bit of an experiment. It's really about us helping each other. I'm hopeful that you'll spend almost as much time meeting each other, meeting your peers and just hearing from the speakers and others. What do we want to do with this now that we've built this together sort of accidentally and organically, what is fundamental about the SAS community is stunning is that CEOs who may even compete with the next generation, everyone founders, all want to share and help. So many deals would get done at Saster where a VC would meet a founder. It might be serendipity, it might be through other programs and they would meet someone here, get inspired by the elevator pitch and have a handshake deal here. Building Saster has been an order of magnitude harder than I ever anticipated. Right when it gets good, it gets complicated. Right when it gets good. There's too many folks coming to the SAS tranual, there's too many sponsors, there's too many speakers. We have 200amazing speakers this year. It's too much to handle. And if you're remotely saying secretly on the side you want to quit, it's the secret thing that founders go through, and you have to find a way to push through it. Sastr is 25 times bigger than it was the first year, which seemed big to be on that journey with the team again in your career. It's a bit unexpected and it's a bit magical. We have to reboot and reinvent every five years, and you have to find it in yourself to do it. And the great founders do. And deep down I think I'm only a very good founder, but I hope maybe this time I can be a great one. We were the first big event that got taken down by Covid, and, yeah, we lost about $10 million all in. I'll tell you what we're planning. We're gonna do Saster Annual. We haven't really announced it, but we're gonna do Saster next year in September. We have the venue, we're gonna move it outside. We decided last week to go full screen forward, invest our limited capital, and we're going. 2021 has already blown out all of our expectations. We have almost 6,000 folks registered here in the vaccinated, tested, screened, outdoor Annual. This is sort of a reboot of Saastr Annual. And so it's almost the first time, the second time. The intuition, the sense is this kind of stuff will be more important when your team is working from home, when your team only sees each other once a quarter, maybe everyone gets together at Saaster Annual from all across the globe next year because this is the great meeting place that would be our dream and hope Saster Annual be the Mecca for a year. When the entire world comes here, have 100,000 people here. In eight to 10 years, the world of cloud will be here. That's a great vision. The whole point of Saster, thousands of pieces of content, years of events, hundreds and hundreds of sessions and podcasts, is to be your virtual mentor. And that's what I needed. There were hundreds of things I wish I'd been told. I wish that the old me, the current me, had told the young me, the young, sassy old me. It's not as far away as you think.
