Episode 682 | The Pros and Cons of Large vs. Small Startup Events

Rob Walling:
This is Startups For the Rest of Us, I’m Rob Walling. This week I talk with Alex Theuma, the founder of SaaStock. We talk about a myriad of topics around trying to bootstrap an event and how hard that is, the pros and cons of large events versus small startup events. And at the end we share a couple memorable mishaps or war stories from years of running events. I’ve actually wanted to attend a SaaStock for the past few years, and there always seems to be a scheduling issue on my end that has kept me from attending. Just to check it out, a big event with a lot of people, multiple stages to see and experience what I’ve heard a lot of folks talk about. So hopefully this episode of the show brings you some insight, some inspiration, and maybe a little motivation to check out SaaStock in the future. 

Before we dive into the episode, I wanted to let you know about our MicroConf Mastermind program. If you listen to this show, you know that I’ve talked a lot on this podcast about how important masterminds have been to my own success. But finding the right founders for your mastermind group can be very hard. Over the past few years, my team at MicroConf has successfully matched more than a thousand founders into mastermind groups by looking at revenue, team size, strengths, goals, and several other data points to make sure your peer group is the right fit. Once you’re matched, you’ll also have access to our mentorship series, a three-month program where you can connect with some great minds in sales, business development, marketing, and more. If you’re looking for accountability, honest feedback about your business and the opportunity to make new friends that care about your company and your success, you can learn more at microconf.com/masterminds. Alex, thanks so much for joining me on Startups For the Rest of Us.  

Alex Theuma:
I am very excited to be here, Rob. Thanks for having me.  

Rob Walling:
Absolutely. It’s a long time coming and as folks heard in your intro, you’re the founder of SaaStock, which I think is interesting overlap with MicroConf, or not even overlap, but just we’ve traveled such a similar path in building our events. And this podcast SPR out of a blog that became a, should we all get together in a room? So we started a MicroConf in 2011 in Las Vegas and it seems like from what I know about your story, perhaps you have similar early stages. And for folks listening, we’re going to talk about SaaStock. Really, I like inside baseball. 

You’re an entrepreneur and a founder, and that’s what this show’s about, is being an entrepreneur and founder. So we’re going to hear stories about things you’ve learned, missteps, even just thinking about bootstrapping a SaaS, we talk a lot about. How the hell do you bootstrap a conference? Just so few of us do it, right? So with all that said, I’d love to hear the early stages, how did you bootstrap a first event and get people to come? Because when you don’t have a brand name, no one will give you the time of day. People are not buying airline tickets and they’re not booking hotels.  

Alex Theuma:
Yeah, yeah, yeah, good question. Yeah, I think we’ve traveled an almost identical path in building MicroConf and SaaStock, right? So you’re right, it came from a blog. I started a blog called SaaScribe in 2015. The idea there was to create a community driven blog for SaaS founders that are growing their businesses, SaaS companies that are growing their businesses. I thought I identified a gap in the market there and to get some experts and influencers to create some content as I’d never run a SaaS business myself, so I’m not the authority to tell people how to do it. So instead, I recruited people to write content for us without charge. I mean as in I didn’t pay them anything. They did it for the good of SaaS and we get their name out of there and they bought into the why. So we had the blog and three months later it kind of took off a little bit. 

It resonated, I was getting a lot of emails from people saying, “I like what you’re doing. I’m rooting for you,” this sort of thing. Three months later, I started the podcast, The SaaS Revolution Show, which is happening still eight years later. And then a few months later, then I started doing local meetups, and it was then when I was having the face-to-face conversations that people were saying, “Hey, look, we’d like a bigger thing.” We’ve got 120 people here today in one of the meetups, which was great, and people travel from all over the UK. It’s like, “We’d a big thing in Europe and you seem to be the person that is probably primed to do it.” I was like, “Oh, really?” Yeah, I’m looking for a way to get into this full-time because I was really enjoying it. I had a side hustle… well, that was the side hustle. 

I had a full-time job, but this was the thing I was trying to explore as to could this help me become the entrepreneur that I finally wanted to become after many years of issuing many ideas. And so that groundwork, I think to your question about how do you bootstrap it and get the credibility and authority. It was from doing the blog posts or running the blog, getting on people’s radar, interviewing founders on the podcast and VCs, that enabled me to have a little bit of authority and credibility. To the point where I think it was in November, maybe a little bit before in 2015, where I met with, I think it was Nick from ChartMogul at the time and their business subscription metrics platform for SaaS businesses. And I had a conversation with him at another conference, I believe it was Web Summit, and said, “Look, people want me to build this SaaS conference in Europe. I’m thinking about doing it.” And he said to me, “Look, if you do it, we will sponsor.” 

I didn’t forget that. And then I kind of went forward with the project. I was starting to build the website, I found the venue, I found the date. As soon as I had that, I went back to Nick and said, “You said you were going to be my… sponsor this, I’ve got a date venue. It’s happening in the RDS in Dublin.” And he came back and said, “Yep, we’ll do that.” And he put his money where his mouth was and became our first sponsor. Maybe one month later, I closed a deal with Patrick Campbell, who was the main competitor, ProfitWell, of ChartMogul. And effectively from there, we were customer funded bootstraps from that point on. And when we started selling tickets in January, so we waited over the Christmas period, the audience was the people that had come to the meetups that was subscribing to the newsletter, reading the blog, that was listening to the podcast. 

And so there was an active audience there of people that had wanted and asked for this conference. I think the first day we sold like 37 tickets, and I saw this spike of revenue and I was like, “Great people actually do want this thing.” So that enabled me to have the runway really to I guess build this for the next nine months and pay myself and then eventually start to bring some other people onto the team. But there certainly were a couple of months where it was very close coming to the end of the month where I was running out of money and I was like, “Oh, I’m not going to be able to pay myself next month.” And then suddenly you get a deal in at the end of the month and like, “Phew, stress over, I can feed the family.”  

Rob Walling:
Right. Well, it seems like you were ahead of us when we started because I didn’t realize that most events, all events need sponsors in order to make them happen. I was under the impression that, “Oh, when people charge a thousand dollars for a ticket or $500 for a ticket, they sell those tickets and that pays for the event.” But no, they’re all subsidized by sponsors and without sponsor subsidy, you have to charge way more. The events are just much more expensive. And so we figured that out the first year and then the second year realized that we’re going to sell sponsors. But you were ahead of that game. It sounds like the sponsor was the first thing. I wonder if that comes from being… because your background is in sales, right? Like enterprise sales?  

Alex Theuma:
Yeah. Yeah, I think so. When I left sales or selling other people’s software, I was like, “Oh, so glad to see the back of sales. I’m done 11 years of sales, I’m done.” But obviously the first thing that I had to do as an entrepreneur was sales and generate revenue. So I wasn’t quite done, but it was quite different when you’re selling your own product and it’s something that you passionately believe in, and also you had to make it work, right? Because I left my job to go all in on this. Gemma, my partner was six months pregnant or something like that. We had no income in the household, so I had to make it work. 

So there’s nothing like something like that to give you that drive, a deadline of knowing when you’re going to run out of money. So I got into it and just I guess through the conversations… And I can’t really remember Rob, whether it was a real deliberate strategy, but to go after the sponsors first. But it just so happened that I had that conversation with Nick, which then gave me, I think it was like 12,000 euros or whatever, to then plot on for the next few months. And then again started to get that in, and I think we ended up or I ended up doing about 35 sponsorship deals for the first year. And it was about 50/50 revenue on sponsorship and tickets for the first year.  

Rob Walling:
That’s incredible. Wow. And there’s this old saying, “Start an event, they said. It’ll be fun, they said.” After we ran the first MicroConf, closing party night, I was telling everyone, “Never doing this again. This is it for us.” For us, it was a side project. We bootstrapped it, we made money on it, made thousands of dollars that first year, but it was definitely not something that I wanted to do again because of how stressful and how much work it was. And I was like, “I cannot justify this.” So then people were like, “No, you have to do it again. This was the best event I’ve been to.” 

It really resonated with the folks. I mean, our first event was 105 people. It was a very small event. So I’m curious to hear your experience of, for you, after running that first event, were you wide-eyed, like, “Oh my gosh, this was so much more complicated and difficult than I thought it would be.” Or did you go in eyes wide open in the sense of, “Yeah, it’s going to be tough.” And when you came out the other end, you’re like, “Well, we broke even or made some money. That’s a big win and we’re going to do it again next year.”  

Alex Theuma:
Yeah, good question. It sort of makes me smile because certainly the first event, I was walking around super tight. I didn’t sleep the night before. I think I actually probably had a panic attack the night before. And in largely, I think it was because we did lose a good amount of money, it was about 60,000 pounds, something like that. And I was like, “Okay, well, we’ve lost all the money. I’m aware I’ve lost the money. How am I going to pay that back?” And so I didn’t sleep very well at all. And then I went to the event and then the event was running, so the event was running kind of without me. After I’d done the opening remarks, you’ve got the production company that’s running the event. Everything seemed to be working fine. I’m walking around speaking to people and everybody’s like, “Alex, you look terrible. You look terrible. Are you not having a good time? You look terrible.” 

Without them knowing the reason that I looked terrible was because I hadn’t slept the night before because I’ve lost this money. But when the event was done, everybody, I remember having a pint of Guinness outside the RDS and speaking to people and just trying to come to the terms with, “Okay, we’ve lost money. We need to figure this out.” And everybody was like, “This is amazing. What’s the plan? Next year double in size, do this, et cetera, and so on.” And I was like, “Well, look, I know one thing for sure is I’m not taking a holiday tomorrow. I need to go back to the sponsors and start selling them on next year again.” And that’s pretty much what I did. So over the next 30 days, I rebooked about a hundred thousand pounds worth of repeat revenue from the sponsors. 

And then that gave me a little bit of, more peace of mind around how I can pay back some of the loss from this cash in the bank as such, and then just repeat. And that’s what we did. We basically, I put the finger in the air and said, “Let’s double in size next year.” And we almost doubled in size year-on-year. And again, it was just another 12 months of hard work and actually 12 months on one event, you don’t need to do that, right? We’re kind of now more on a six-month cycle per event, but I used to spend 12 months, five tweets a day than doing… you’re kind of doing everything, recruiting the speakers, doing the sales. That’s what you had to do for the first event. Now I’ve got a team of people doing that, so you don’t need to work six months on it.  

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So I want to ask you a bit about your thoughts on pros and cons of event size or event type. And the couching of this question is most people listening to this podcast are familiar with MicroConf, our flagship event in the US. It’s in Atlanta here in April. It was in Denver last April, and then we have a flagship Europe event. It’s in Lisbon actually in a couple of days as we’re recording this. We are single track, we are 150 in Europe and we peaked at 300 in the US and then COVID, so now we’re at about 250, I think Denver was, and hopefully Atlanta will be that as well. And we have five or six speakers and we have a lot of activities and networking and this and that, two and a half day event. 

And there are certain pros and cons of that format. The pros, it’s super intimate. There’s a lot of other stuff versus a SaaStock, which I think you were saying it’s several thousand attendees, it’s multiple stages. There’s a bootstrapper stage, there’s a venture stage, a growth stage, whatever, all these different tracks. In your mind, what are the pros and cons of that model, of these contrasting these two models? Because I don’t believe either one is better than the other, but I do wonder as someone who runs a big event and has now for many years, how do you think about that?  

Alex Theuma:
Yeah, it is a good question. I guess from the very first SaaStock, I did think about how do we grow this? I wanted to have a growth business and not just have the conference that… and there’s nothing wrong with this, but that was kind of the same size doing the same revenue each year. I wanted to think big, but also I think during every single event, and certainly in the early years walk around and people are saying, “This is the perfect size at 700, don’t grow any bigger.” At 1500 they said, “This is the perfect size, don’t grow it any bigger.” And I think they stopped-  

Rob Walling:
We get that too.  

Alex Theuma:
Yeah, they stopped-  

Rob Walling:
We get that at 150.  

Alex Theuma:
Yeah, they stopped saying that. Well, 150 apparently is the perfect size where people, everybody can connect with each other, right?  

Rob Walling:
It’s Dunbar’s number [inaudible 00:14:56].  

Alex Theuma:
Yeah. You certainly sort of lose that at SaaStock, but by design, I’ve always thought, “Okay, as we scale the event, how do we keep the people happy that perhaps smaller events and what do we do there?” So there’s a lot of curation and actually SaaStock, if you deconstructed it, could be many mini events and one big event put together. So on the first day we do this thing called SaaS City, which is a one-day accelerator for your SaaS. I think this year it’s about 10 different workshops with probably 50 to 60 people per workshop. Then we do pub crawls, and then there’s an opening party with about a couple of hundred people. So with the workshop sort of size, there’s nothing really daunting about sitting with 50 of your peers in a day long workshop that’s being led by some of the best experts in the industry. 

Then at the main event itself, that’s when it gets a little bit more of the scale, but then we look to have all these different stages in terms of content for everybody. So like you said, the bootstrapper stage, that’s a stage for about 150 people. And again for an audience of bootstrappers and generally those that are doing anything from zero to a hundred million. But I would say the majority of our speakers will be under 10 million in revenue and be sharing stories of how they got to 10 million. We’ve got a few, Gregory, I can’t remember his surname, the CEO of MuckRack, they’ve got to 50 million ARR. Great to be able to share those kinds of stories as well. We have an accelerate stage, again, for those that are really just at that really early traction stage. We’ve got the expo, which is obviously a big part of it and the showcase. 

And then what happens, there’s a bit of an ecosystem that’s grown around SaaStock now. So last year, as far as I knew, there was about 20 different side events that are happening around SaaStock in various parts of Dublin. And that includes actually, and I don’t know necessarily how I feel about it, but I think more positive is that people are running their own events. Well, SaaStock is on to capitalize on the fact that we’ve got the audience there and we’re not getting any financial benefit from that. But actually having more side events, I think, and a bigger growing ecosystem, I think really does add value and gravitas to the event. So there’s con there that we lose a bit of sponsorship revenue potentially and that they’re taking the audience out of our venue. But the pro is I think the more side events, so I believe it kind of helps with the gravitas of the event. 

But pros and cons in terms of size, well, I think certainly a con, if we start with that. For some people it can be overwhelming and if you maybe be more of an introvert or not a natural kind of networker, perhaps it can be a little bit overwhelming. When you come in and there’s a buzz, there’s the noise, there’s thousands of people, it’s like where do you start? And maybe you start with just watching a bit of content. But we do try to facilitate all these connections through our smaller events and through the networking app and so on, so you can meet the right tribe. We also do lots of dinners, smaller dinners, whether you’re like CMO, CFO,-CEO, sort of dinners, et cetera, to put people together as well to kind of help with that. I think someone like the pros, if you are used to a smaller event and single track, obviously there is much more I think available if you’re looking at a menu, a la carte menu, you can pick and choose what you want and where to go and what talks to see. 

And even if you’re a bootstrapper, watch a few talks in the bootstrapping stage, but pique your curiosity to look at some of the venture backed companies that have made it to a hundred million and sort of consider. I’ve had a number of conversations with those that are really anti VC over the years, would never take VC money and bootstrap to 30 million in revenue and then finally took VC money. And I don’t know whether they’re happy or not about that, but they did some secondaries and stuff like that. But people do change, and I think SaaStock gives you that optionality to think about that and say, “Well, maybe bootstrapping is right for me now. Maybe we can change in the future and I can speak to VCs, get feedback on the product and so on.” 

So there’s a few things there, but I think there’s a lot, the main pro is a lot of optionality, and you can just do the small stuff if you just want to do the small stuff. But I would always say spend some time before you go to the event and be prepared. I think if with a 150 person event, you could probably just rock up and ideally almost speak to everybody there and not do too much kind of prep. And with an event SaaStock, try and figure out who you want to meet, what talks you want to see, carve out your own agenda. And that’s the benefit of having all these options that you can create your own agenda and not just the one that we put on.  

Rob Walling:
And as someone like yourself who is programming these events, I know you have a team doing that. And when I say program, I mean you pick the speakers and you help them figure out what to talk about. And so you are in essence a taste maker, just like being, you have a podcast, you have a blog, you can set the agenda of what a lot of founders here just like this podcast does and MicroConf does. And I’m always pretty deliberate about what do I think people need to learn this year? And sometimes there’s fortuitous like, “Oh, I recently heard about this amazing speaker and whatever they speak about is going to be great.” 

But oftentimes it’s like, “I think this is a pertinent thing that founders aren’t thinking enough about.” So maybe five years ago or three years ago, it would’ve been like, “People should know enough about Web3.” They don’t want to be sick of it, but I think SaaS founders should know enough. So there should be a talk about that, for example. MicroConf didn’t do that, but AI may be a thing, a topic of today or whatever. I’m curious how you think about that. What do SaaS founders need to know? How do you know what they should maybe be learning at this event?  

Alex Theuma:
Yeah, yeah, good question. So yes, we do have a team that does that. I still advise, and I still use my position to email and book speakers and do introductions and so on. But effectively in terms of our process, so let’s say after one conference finishes, part of the processes that we get on customer calls and get feedback and what did they like, what didn’t they like. And then there will be a sort of research process in terms of what are the current topics for the year and for the agenda. Ahead we will put a steering committee together or a mixture of VCs, bootstrap founders, some operators, and the person who runs our content program. And David will speak to these folks on a regular basis and say, “Who should be speaking? Who are you following? What topics should we be covering? What are you seeing out there in the market?” 

And gathering this data and then compiling this data to then give us a list of options of these are the topics, these are the themes. We also survey our attendees post customer research calls to ask them what are their biggest problems that they’re facing? And if we see a commonality in trends, then we say, “Okay, well look, if you’re saying your biggest problem is fundraising, if we put a lot of content on fundraising and solving this problem, hopefully there’s a real compelling reason for you to come to the event, right? Because we’re actually talking about problems that you have and how to solve them as well, right?” So I think it’s these things and then you mentioned AI, for instance. So definitely we’ve got… actually one of the topics is AI, we’ve got workshops on generative AI. I think it just makes sense. 

It’s certainly one of the buzzy things this year, it’s super topical. We have been to conferences this year, which are similar to ours where AI wasn’t mentioned at all. It’s just the typical, here’s how we got to 200 million stuff, which was still good content, but actually not talking about what’s happening today and in the future and what people need to be considering. So we do need to do that. We haven’t always done that, process hasn’t always been there, but now that’s a little bit of the insight to what it looks like. And just to ensure that we’re not missing any elephants in the room there and just kind of covering the things that people want to hear about.  

Rob Walling:
Last question as we wrap up. I have some more stories from MicroConfs. I’m not going to mention names, but we have had a bottle of hot sauce thrown at a speaker while they were on stage. We have had a sprinkler go off in the middle, of lights heated it up, it went off in the middle of the event, people running out. I have t-shirts made with these things on them, if you know you know, there are others. We had an MC fall off the back of the stage while she was MCing. We have a great audio of that. I mean all these are crazy scary when they happen, but then they make the stories. Just like growing a SaaS company, you get these stories of the crazy customer, the time Russian hackers invaded your this and that. I’m curious, as we wrap, if you have one or two of those, again, no need to mention names, but just some crazy stories because it’s inevitable I think as you run events like this that those happen.  

Alex Theuma:
Yeah, yeah. I would say no major disasters that I’m aware of, but one from last year was interesting. I don’t know if it’s a crazy story, but our friend Patrick Campbell, he did a talk where all he said was the word churn for 20 minutes.  

Rob Walling:
I’ve heard about this.  

Alex Theuma:
Yeah. And it really divided-  

Rob Walling:
There were mixed reviews, weren’t there?  

Alex Theuma:
Really divided audience.  

Rob Walling:
Because it was like an art piece.  

Alex Theuma:
Yeah, yeah, yeah. So the slides were really good, but people were just like, “Yeah, is he really doing this?” And the room was packed, right? But shall we say, I think the majority didn’t really like it too much and we’re not repeating that, but it was bold. We also kind of knew it was going to happen and we’re like, “We’re not sure if you should do that.” But we went with it anyway. So I think that’s one that was pretty interesting and bold by Patrick. And that’s not the reason he’s not coming back this year, but he’s obviously sold his business to paddle and I think he’s busy doing other stuff.  

Rob Walling:
Pretty busy, yeah, I’ve chatted with him.  

Alex Theuma:
Another quick story. I think this was probably like 2019 or 2018, but we do speaker dinners and I have to do two of them. I do one on Monday for the speakers on Tuesday and one on Tuesday for the speakers on Wednesday. So it’s quite a lot of food and often a little bit of alcohol consumed, although I’ve been a bit better at that. Certainly last year after one of the speaker dinner, perhaps on the Tuesday night, went on until midnight and then a good group of us then went on somewhere else. And then before I knew it was probably about 3:30 AM and I found myself with a bunch of speakers who were speaking the next day doing shots in a local nightclub, not feeling great when we were doing the shots. 

And then we probably rolled in about 4:00 AM. I had to be on stage at like eight 30 with one guy that was with me. I could barely open my mouth, it was so dry. And he was fine, he was finished, he was just like… it didn’t affect him whatsoever. And then one of the other speakers that was with us, he then had to speak that morning. I saw him after his talk and he said he vomited at the side of the stage and then one of the other guys that was with us turned sober after that experience. So it was some night. And then I did think to myself, “Is it responsible for me as the conference organizer to be out drinking with the speakers at that time in the morning?” So I haven’t repeated it, shall we say.  

Rob Walling:
Yeah, it’s an interesting thing because, I’ll admit, the first few years of MicroConf, I would often stay up till 4:00 AM 5:00 AM with people because it’s so fun and you’re hanging out and then it would take its toll. I never did it with speakers, I would’ve always been like, “Oh no.” But you do learn these lessons. In retrospect, it’s like obviously you don’t want to do that, but you’re in the moment and you’re hanging out and you’re friends and you’re just like, “Oh, we’ll just have one drink.” So I can imagine that makes a pretty incredible story.  

Alex Theuma:
Didn’t happen to us yet.  

Rob Walling:
Yeah, didn’t repeat it for sure. Alex Theuma, thank you so much for coming on Startups For the Rest of Us. Saasstock.com if folks want to see what you’re building and dig in further and SaaStock on Twitter or X, that’s your account. Any other places folks should head to?  

Alex Theuma:
We’re on LinkedIn. I would say we’re pretty active on LinkedIn and a little bit on X, now I’ve got to get used to saying that. But come to saastock.com, the next conference is 16th through the 18th of October in Dublin. If you haven’t been yet, you’ve got to come once in your life.  

Rob Walling:
Sounds great. Thanks again for coming on the show.  

Alex Theuma:
Thanks Rob. Great to be here. Thank you.  

Rob Walling:
Thanks again to Alex for coming on the show, and thank you for joining me again this week. I’ll be back next week answering some listener questions, still trying to get caught up on that front. Talking about things like bringing on a partner, attending trade shows, offering pre-launch discounts and other questions sent in by folks just like you. This is Rob Walling signing off from episode 682.