The Basic Story
Nathan Barry started ConvertKit in 2013 with a simple goal: build better email software for creators like bloggers, YouTubers, and musicians. Today, it's called Kit and makes $43 million every year. The crazy part? He did this all by himself—no outside investors, no rich person giving him millions. Just smart strategy, hard work, and smart choices.
Let's break down exactly how he did it.
The Big Idea
Why Being "Small" Was Actually Brilliant
When Nathan started ConvertKit, email software already existed. MailChimp dominated the market. Constant Contact was popular. Campaign Monitor had fans. Trying to compete directly with these giants was impossible for a new company.
So Nathan made a smart move: he didn't try to beat them. Instead, he changed the game entirely.
He decided ConvertKit would ONLY focus on creators—people who write blogs, make YouTube videos, create online courses, and make music. Not small businesses. Not e-commerce stores. Just creators.
This sounds simple, but it changed everything:
| Market | ConvertKit's Share | Mailchimp's Share | Others |
|---|---|---|---|
| All email users | 0.1% | 30% | 70% |
| Creator-only market | 60% | 20% | 20% |
ConvertKit went from a tiny player (0.1%) in a crowded market to a dominant player (60%) in a focused market.
Nathan Was His Own Customer
Here's something powerful: Nathan used to be a creator himself. He wrote ebooks and made $85,000 in just 4 months selling them online. This meant he wasn't guessing what creators needed—he lived the frustration.
He knew that tools like MailChimp were built for people selling t-shirts online, not for writers trying to build a loyal email audience. That insight was gold.
Early Years
The Near-Death Moment
ConvertKit's first year was rough. Nathan made only $2,000 per month. Within a few months, that dropped to $1,300. For a founder, that's terrifying. Most people would have given up.
But Nathan didn't. In 2014, he spent $50,000 of his own money to keep the company alive. He also made a bold decision: he would personally talk to every single customer.
Unscalable Sales That Actually Worked
Nathan's sales process was slow and exhausting, but it worked:
Step 1: Research creators
Nathan didn't send mass emails. Instead, he found the top creators in specific niches—fitness bloggers, fashion bloggers, parenting bloggers—and learned about their businesses.
Step 2: Ask them what's broken
His first email wasn't "Buy my product!" It was "I noticed you're using MailChimp. What's frustrating about it?" He genuinely wanted to know.
Step 3: Talk on the phone
If they replied, Nathan would jump on a Skype call personally. He wasn't a sales robot reading a script. He listened.
Step 4: Remove the biggest barrier
Here's the killer insight: Most creators wanted to switch to ConvertKit but didn't want the hassle of moving their email list, automations, and forms from MailChimp. It was too much work.
So Nathan did something crazy—he offered to do it for free. He would manually export their data, rebuild their automations, and set everything up. Even for customers paying only $29 per month. For free.
This sounds like a losing strategy (he spent hours of his time on each migration), but it removed the biggest reason people said "no." And it worked.
The Results
By December 2015, ConvertKit was making $19,000 per month. That's a 15x increase from the $1,300 low.
More importantly, those early customers became huge advocates. They felt genuinely cared for—because they were. They told their friends.