Rob Walling

That's the gap in this market. And so Paul Graham talks about knowledge gaps. I actually think there's positioning or kind of market gaps. And then what we learned after we launched is that there was actually a massive gap in marketing automation, which is a term I had never heard, didn't know what it meant.

That's the gap in this market. And so Paul Graham talks about knowledge gaps. I actually think there's positioning or kind of market gaps. And then what we learned after we launched is that there was actually a massive gap in marketing automation, which is a term I had never heard, didn't know what it meant.

And people started saying, hey, are you trying to unseat these big marketing automation providers? Like Infusionsoft, Marketo, Pardot, Silverpop, there's a bunch of others. But what we now know today as just email marketing was much simpler back then. And so it took me a while to wrestle with this, to reorient the company around, we are going to become a lightweight marketing automation tool.

And people started saying, hey, are you trying to unseat these big marketing automation providers? Like Infusionsoft, Marketo, Pardot, Silverpop, there's a bunch of others. But what we now know today as just email marketing was much simpler back then. And so it took me a while to wrestle with this, to reorient the company around, we are going to become a lightweight marketing automation tool.

But eventually I decided what I wanted to work on. And then I had to educate myself on marketing automation. I had never used any of those marketing automation tools. I had never even logged into one. And there were folks like Brennan Dunn giving me advice because he, I believe, had an Infusionsoft account. Keith Perhak had an Infusionsoft account.

But eventually I decided what I wanted to work on. And then I had to educate myself on marketing automation. I had never used any of those marketing automation tools. I had never even logged into one. And there were folks like Brennan Dunn giving me advice because he, I believe, had an Infusionsoft account. Keith Perhak had an Infusionsoft account.

He's a founder of Stagmetrics, now funded by TinySeed. And I remember literally emailing him saying, we're thinking about building these automations. How do they work in Infusionsoft? Infusionsoft, by the way, renamed itself Keep and they recently sold to private equity for less than 1x ARR multiple because they didn't have, they just stopped growing.

He's a founder of Stagmetrics, now funded by TinySeed. And I remember literally emailing him saying, we're thinking about building these automations. How do they work in Infusionsoft? Infusionsoft, by the way, renamed itself Keep and they recently sold to private equity for less than 1x ARR multiple because they didn't have, they just stopped growing.

They weren't releasing software fast enough and they didn't keep up with the market. Product market fit drifts. And so what I realized was, and it was hard, I mean, it was a hard realization. I'm not saying in retrospect, I was 100% and I knew it was just this amazing thing that I was totally convinced of.

They weren't releasing software fast enough and they didn't keep up with the market. Product market fit drifts. And so what I realized was, and it was hard, I mean, it was a hard realization. I'm not saying in retrospect, I was 100% and I knew it was just this amazing thing that I was totally convinced of.

I was trying to learn enough about it to get to the frontiers of knowledge and I was noticing the knowledge gaps. And the knowledge gaps in this case were they were positioned upmarket. They were charging way more money than you needed to to still make a lot of money as a software company. And their sales process was terrible. They locked you into one-year contracts.

I was trying to learn enough about it to get to the frontiers of knowledge and I was noticing the knowledge gaps. And the knowledge gaps in this case were they were positioned upmarket. They were charging way more money than you needed to to still make a lot of money as a software company. And their sales process was terrible. They locked you into one-year contracts.

They had a mandatory upfront $2,000 fee. People hated it, but there was no alternative. And at the time, I didn't want to build a marketing automation platform. I didn't really know what it was. It sounded really boring. It sounded like a lot of work. To be honest, I've never been afraid of hard work, but I thought that it would be a tough business.

They had a mandatory upfront $2,000 fee. People hated it, but there was no alternative. And at the time, I didn't want to build a marketing automation platform. I didn't really know what it was. It sounded really boring. It sounded like a lot of work. To be honest, I've never been afraid of hard work, but I thought that it would be a tough business.

There was a lot of competition and there were a lot of things going on in that space. And so Paul Graham's fourth step is boldly chase outlier ideas. Now, let's be honest, Drip is not nearly as much of an outlier idea as Uber is. or WeWork, or even Stripe, or Facebook, or Google, right? There's different levels of outlier idea.

There was a lot of competition and there were a lot of things going on in that space. And so Paul Graham's fourth step is boldly chase outlier ideas. Now, let's be honest, Drip is not nearly as much of an outlier idea as Uber is. or WeWork, or even Stripe, or Facebook, or Google, right? There's different levels of outlier idea.

But eventually, I did a ton of soul searching, and I came to grips with the fact that pivoting, drip, and ad becoming full-blown email marketing was already in the works. Derek and I had talked a lot about that, and it just made sense. It's like, oh, we can, I think that's a legit... need in the market.

But eventually, I did a ton of soul searching, and I came to grips with the fact that pivoting, drip, and ad becoming full-blown email marketing was already in the works. Derek and I had talked a lot about that, and it just made sense. It's like, oh, we can, I think that's a legit... need in the market.

But the idea of going full-blown into marketing automation and adding all the automations and the triggers and the actions and all that was something we really had to wrestle with. That's just one example.

But the idea of going full-blown into marketing automation and adding all the automations and the triggers and the actions and all that was something we really had to wrestle with. That's just one example.