10 Years of SaaStr | SaaStr Software Community

Jason M. Lemkin built EchoSign, which Adobe acquired, then created SaaStr by answering SaaS questions on Quora. The annual conference grew from 1,600 attendees in 2015 to 40,000, but COVID cost the organization $10 million. He's rebuilding it as an outdoor, vaccinated event in September 2021.
Chapters
I was a founder myself. So 2 startups, the last one a company called EchoSign that Adobe acquired. Real story of the community is when I was a VP at Adobe, there were 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 a 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 Quora. So it turned out today we crossed 1,300 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'd had figured out all the applications were built, marketing automation, sales automation. It was kind of a stable time to where we would grow like this. Instead, boom! With about 60 days notice, we did the first SaaStr Annual in 2015, and over 1,600 people came. I should have realized that meant we had initial traction and scale. To have Aaron Levie and Stewart Butterfield and other leaders come when there had never been a community event for SaaS. 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, than 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 SaaS 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 SaaStr 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 SaaStr 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 SaaStr Annual. There's too many sponsors, there's too many speakers. We have 200 amazing 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. Zaster 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. You have to reboot and reinvent every 5 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 going to do Saastr Annual. We haven't really announced it. We're going to do Saastr Annual next year in September. We have the venue. We're going to move it outside. We decided last week to go full steam forward, invest our limited capital, and we're going for it in September. 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 Saastr Annual from all across the globe next year because this is the great meeting place. That would be our dream and hope. SaaSter Annual be the mecca for a year when the entire world comes here, have 100,000 people here in 8 to 10 years. The world of cloud will be here. That's a great vision. The whole point of SaaSter, 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 SaaS CEO me. It's not as far away as you think. [MUSIC] [MUSIC]
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