Nicolas Cole tried building a paid newsletter in 2019 and found the tools broken. He spotted Substack solving that exact problem, got rejected as an investor, then built two newsletters there instead. Category Pirates hit six figures in revenue.
Christmas of 2019, I had just scaled down my ghostwriting agency and I decided, you know what would be really cool is I would love to start a paid newsletter. And so I spent, I remember Christmas Eve, Christmas Day, like at random times, I was trying to duct tape together all these different tools because I wanted to launch a paid newsletter. So I needed one platform to handle the newsletters, but I needed to find another platform to process the payments. 2019, we forget or take for granted how fragmented a lot of these tools were even just 5 years ago, 6 years ago. And so I tried launching this paid newsletter and I got it to work, but it was It was so janky. Maybe 6 months, 12 months later, I see that Substack raised its first round and they raised like a meaningful first round. And I remember seeing that and going, "I have lived this problem 'cause I just tried to start a paid newsletter and it was difficult." So when I saw them do their thing and they made the whole category paid newsletters, this is the future, instantly I got it. I emailed the founder and was like, "Can I be a strategic angel investor? Please let me be part of this." They had already closed their round. They said, "No, unfortunately." And I was like, "All right, well, at a minimum, I'm going to use your platform." And I would love to give you feedback and ideas along the way. And since then, I've communicated with their team a lot and I've beta tested new features. We ended up launching two really big paid newsletters on their platform. The first was Category Pirates. I scaled that to mid-six-figure paid newsletter there. And then the second, which is now one of their top paid education newsletters, is Write with AI. And I started Write with AI back in 2023 when I started to see Substack was really doubling down on, we're raising more money and we're going to start to turn this into a social ecosystem. Which now they're calling Notes. The moment I saw that, I was like, I watched this happen with Quora. I've watched this happen with Medium because I was early on Quora and I was early on Medium. And I was like, I know that you only raise that much money if you're committing the next decade to this platform. And so you just follow the money. And I doubled down on Substack and I'm more bullish on Substack than I ever been.
What Every Writer Gets Wrong About Their Audience #writing #creator #writingtips
