How My Bootstrapped Startup Turned into a $140K AppSumo Launch

Earlier this year, we spoke with Benjamin Dell, the founder of Missinglettr, HelpShelf, and HeySummit to chat about marketing, funding, copycats, and how to successfully sell SaaS businesses.

But towards the end of our conversation, something a bit magical happened. 

When I asked, “What’s your approach to marketing a bootstrapped SaaS product?” Ben told us the story of how a simple marketing idea for Missinglettr resulted in launching a brand new startup. A platform called HeySummit.

Here’s how he did it:

What’s your approach to marketing a bootstrapped startup?

Ben: “My philosophy is that you want to maximize impact in as little time as possible. When you start to think in those terms, you’ll quickly realize you need a multiplier effect — that is to say, a relatively small amount of effort that results in a large enough result on the way out. If you can automate any of that as well, all the better. 

But this is not necessarily how you think if you’re VC funded. When you go the VC route, you’re looking for multipliers in terms of revenue, sure. But this often translates to spending loads of cash on paid acquisition and everything else that comes with it. 

In the self-funded world (the world I inhabit), you’re looking for the most bang for your buck in terms of effort put in. Combine this with the fact that I often can’t afford to spend 6 months or longer on exploratory projects or ideas. I need results now.

I’ve worked with this mindset for 10+ years now, and it’s really focused how we do everything.”

The story of HeySummit

Ben: “It all started when I decided to put on a conference for Missinglettr last year. 

Running an online conference is an incredible way to get in front of tons of people and get a lot of exposure. It ties into the type of marketing activity that’s best for bootstrapped SaaS companies. 

In my case, it also resulted in creating a whole new business. 

In late spring of last year, with summer approaching, I knew that Missinglettr development would be slowing down. No big updates would be coming out for a couple months. 

I knew that I wanted to engage with our customer base to keep them interested, engaged, and excited. 

So over a 2-3 week period, I decided: let’s find an expert in some related field (email marketing, social media, blogging, etc.) and have them do a webinar for our customers. I simply wanted to deliver value to our amazing customers. 

That’s how I left the idea before going to bed that night. When I woke up the next morning, I realized that the idea wasn’t anywhere near ambitious enough — not for my liking anyway.

Fast forward about 30 minutes, and my idea had transformed into ‘Why don’t we instead put on a two-week summit and create a proper online conference? Not just one a week, but a solid two-week program. Let’s not just follow the status quo and pick 2-4 people to speak. Let’s instead choose a nice round number, something that has a ring to it — something like 100 speakers in a two-week period. Yep, that sounds nice — and feels like a good challenge.’”

When I woke up the next morning, I realized that the idea wasn’t anywhere near ambitious enough — not for my liking anyway.

Ben’s 100-speaker online summit

Ben: “So with that decision made, I now found myself with just 6-8 weeks to find 100 speakers, plus attendees and sponsors to make some revenue. Two days in though, I discovered something that would massively change the course of this project. 

In short, it quickly became clear that there wasn’t a single solution, platform, or product that would enable me to deliver an online conference at this scale. To be honest, there wasn’t even a tool out there that would let me deliver a conference with just 1 speaker, let alone 100!

Sure, there were 10,000-word blog posts explaining all of the tech that would need to be stacked in order to run an online conference. It was ridiculous. All the advice out there was overly complicated and ultimately would result in a pieced together solution that would just look miserable from a branding standpoint. 

It would cost us thousands of dollars to get a designer and developer to do a ton of work even though it was just a WordPress template here, and Mailchimp over there. And we would have to repeat it all in one year’s time. It felt so against my principle of automating and creating efficiencies in how we deliver things.

And so very, very quickly this whole idea turned from three talks in three weeks to 100 speakers over a two week period. We decided we would do all that and build the platform it would run on. 

But not only that, I decided that I couldn’t disrupt my Missinglettr team, so I took 100% responsibility for the whole thing over that 8-week period.” 

In short, it quickly became clear that there wasn’t a single solution, platform, or product that would enable me to deliver an online conference at this scale.

The first summit

Ben: “So we put on the event: We had 3,500 attendees. Made about $10,000 in sponsorship revenue. Nothing crazy, but considering we only had 8 weeks, I’m pretty happy with it. 

All our speakers presented live. (Except one who had double-booked with his wedding! We let him pre-record his session.) 

It was a crazy experience: I would wake up at 6am, fix things that we noticed the night before. The first talk would go live at 2pm. Then for the next 8 hours I would host talks. Finally I’d upload the recordings and the platform would send them out as replays. 

Apart from hosting the live talks and editing the replays, the platform did it all. And boy, did it do it well! On the frontend, attendees saw an incredible platform delivering content across a range of categories and speakers. We even had Ilona Abramova, Head of Content at AppSumo, give a talk as well. 

But behind the scenes, I was working frantically to get everything out and keep everything running smoothly.”

Results & findings 

Ben: “Crucially, at the end of it, we realized, ‘Damn, there’s a product here that has enabled us to do all these wonderful things.’ 

Our speakers loved that they could log in, update their own information, and see in real time how many people were registered for their talks, broken down by demographic and country — data that they’d never seen before when speaking online. 

So it became very clear that there was an opportunity to spin this platform out into its own business. So that’s what’s been consuming my time since then. 

6 months after launching, we decided to run the HeySummit deal through AppSumo. And that’s when things really started heating up.

Our two-week deal with AppSumo netted $140K and resulted in $100,000+ additional ARR. 

So that’s the case study: how a marketing idea for my other SaaS company Missinglettr resulted in the idea for HeySummit — and how we launched it as a business in its own right.”