| $1,207 | $45M | $5,000 | 5 |
| MRR at the lowest point — October 2014 | Annual revenue today (now rebranded Kit) | Initial investment Nathan allowed himself | Decisions that changed everything |
$1,207. That was ConvertKit's monthly recurring revenue in October 2014 — after 22 months of work, a $5,000 personal investment, and a public challenge Nathan Barry had announced to the entire internet.
A respected startup advisor told him directly to shut it down. The graphs weren't just flat — they were going backwards. His books and courses were making $250,000 a year without this kind of effort. The logical decision was obvious to everyone watching.
He didn't take it. What happened next is now a $45 million per year business. But the interesting part isn't the outcome — it's the five specific decisions Nathan made that contradict almost everything the startup world tells founders to do. Each one looked wrong at the time. Each one turned out to be exactly right.
What We Cover
- Decision 1 — He ignored the advisor who told him to quit
- Decision 2 — He shut down his profitable business to save his struggling one
- Decision 3 — He niched down when every investor said the market was too small
- Decision 4 — He did $5/hour work to close $500/month customers
- Decision 5 — He gave away the one thing competitors charged for
- What I Learned From This Startup Story
- FAQ
Decision 1 — He ignored the advisor who told him to quit
The thesis: Good advice is not always right advice — and the decision to ignore it can be the most important one a founder makes.
What happened: At a conference in late 2014, Nathan ran into Hiten Shah — co-founder of KISSmetrics, one of the most respected voices in SaaS at the time. Shah told him plainly: "Look, you should shut down ConvertKit." Nathan's first reaction was that it wasn't a very nice thing to say to someone who had been working on something for a year and a half.
The advice was logical. Revenue was declining. The product had been live for over a year. No meaningful traction. A more profitable business was running in parallel and demanding attention. Shutting down made sense on paper.
The verdict: Nathan waited six months before doing anything with that advice — and in that time, he found his reason to stay. He asked himself two questions: Did he still want to be the CEO of a SaaS company? Yes. Had he given it his best effort? No. The advisor wasn't wrong about the data. He was working with incomplete information — he didn't know how much Nathan hadn't yet tried.
The lesson isn't to ignore advisors. It's that outside advice is based on visible data. The founder is the only person who knows what hasn't been tried yet.
Decision 2 — He shut down his profitable business to save his struggling one
The thesis: Splitting attention between a working business and a struggling one guarantees both will underperform. Most founders choose the comfortable option — keeping both running. Nathan chose the harder one.
What happened: ConvertKit's MRR had slid all the way down to $1,207 by October 2014. His books and courses were doing great — bringing in $250,000 a year — but ConvertKit was sliding further towards zero. The sensible move was to keep both running: let the books fund the startup while he worked on both simultaneously.
Instead, Nathan shut down his course business entirely. "I'm not good at doing two things at once," he said. "I'm a focused person. I run one business. And hopefully, I do it well."
The verdict: Within months of going all-in, MRR grew 23% in one month, then another 27% the next. From $2,000 MRR in 2013 to $625,000 MRR by 2016 — the growth curve shows sharp spikes that began precisely when Nathan stopped dividing his attention.
This is one of the most uncomfortable startup decisions that exists — deliberately killing revenue you already have to bet on revenue you don't. Almost nobody does it. The data from ConvertKit suggests it works.
Decision 3 — He niched down when every investor said the market was too small
The thesis: When investors tell you the market is too small, they mean it's too small for venture scale returns. That is not the same thing as too small to build a real business.
What happened: When Nathan tried raising capital, VCs passed — the market was too narrow, they said. His response was to go narrower still. He described targeting "professional paleo recipe bloggers who are women" — not food bloggers, not recipe bloggers, specifically paleo recipe bloggers who were women and ran professional operations.
This ran against everything the conventional startup advice says about total addressable market and growth potential. MailChimp served everyone. ConvertKit deliberately served almost no one — at first.
The verdict: "The riches are in the niches." ConvertKit decided early on that they needed to focus on a specific type of customer — and that focus is what allowed them to build product features, messaging, and community that nobody else was offering. The niche was a wedge. The business is now generating $2.1M monthly revenue, has been listed on the INC 5000 numerous times.
The investors weren't wrong that the paleo blogger market was small. They were wrong that starting there meant staying there.
Decision 4 — He did $5/hour work to close $500/month customers
The thesis: Unscalable actions are not mistakes in the early stage. They are the fastest path to understanding what customers actually need — and to getting enough of them to matter.
What happened: The biggest barrier to switching email marketing platforms is the migration process — moving subscriber lists, tags, automations, and sequences from one platform to another. Most companies solve this by writing documentation. Nathan solved it by doing it himself, manually, for free.
He would pull up a prospect's MailChimp account on one screen and ConvertKit on another and copy and paste between them while watching a Netflix TV show — to do all this "$5 an hour work," as he described it — just to get someone up and running.
The verdict: These concierge migrations eliminated friction entirely. Personal demos combined with free migration handling meant that the switching cost — the number one reason people don't change platforms — became zero. Once someone was on ConvertKit with their list fully migrated, they were extremely unlikely to switch again.
This is the Stripe playbook, described by Nathan himself — when the Collison brothers were building Stripe, they would pull out their laptops and help people code payment processing into their app on the spot, at a conference, which was "100% not scalable at all, but absolutely necessary to build things up." Nathan understood the same principle applied to ConvertKit.
Decision 5 — He gave away the one thing competitors charged for
The thesis: Removing the biggest barrier to trying your product matters more than almost anything else in the early stage — even if removing it costs you money you don't have.
What happened: Email list migration was expensive, time-consuming, and anxiety-inducing for creators. MailChimp charged for it, or left customers to figure it out themselves. ConvertKit made it free and handled it personally — every time, for every new customer, regardless of list size.
ConvertKit's team handled setup for free — moving subscriber lists, tags, and automations for new customers. This was the concierge migration strategy that eliminated switching friction entirely. The cost of doing this was significant. The alternative was watching potential customers decide the hassle wasn't worth it.
The verdict: Combined with the affiliate webinar strategy — Pat Flynn hosted a webinar promoting ConvertKit that led to 1,000 sign-ups in just 24 hours — giving away the migration service turned into a word-of-mouth engine. Creators who had a smooth migration experience told other creators. The cost of the free service was a customer acquisition investment, not a giveaway.
Most founders price their time correctly and then price themselves out of early traction. Nathan priced his time at zero in the short term and built a $45M business in the long term.
What I Learned From This Startup Story
Having covered dozens of founder stories on this site, the detail that stopped me in the ConvertKit research was not the revenue number — it was the timeline. ConvertKit's lowest point came 22 months into the business — not 3 months in, not 6 months in, but nearly two years after launch. That's the part nobody puts in the headline. Most founders who quit would have quit before October 2014. The ones who would have stayed past that point are a much smaller group — and that smaller group is where ConvertKit's actual story begins.
The number worth analyzing here is not $45M. It's $50,000 — the amount Nathan invested from personal savings after deciding to double down. He sold investments so he had enough money to live on, cut costs, renegotiated contracts, and increased efficiencies all at the same time. This is not a story about someone who had runway. This is a story about someone who manufactured runway by dismantling everything comfortable in their financial life. That's a different category of commitment than "I quit my job to work on my startup."
The question this story doesn't answer — and I haven't seen anyone ask it directly — is what role Nathan's existing audience played in ConvertKit's eventual growth. He had 30,000 email subscribers before ConvertKit launched. He had credibility in the creator economy before the product existed. He was a successful ebook author who had made $85K in just four months before starting ConvertKit. The five decisions I've outlined above are real and repeatable. But the distribution advantage that came from being Nathan Barry specifically is not repeatable. Founders reading this should apply the decisions — and be honest with themselves about the audience head start they don't have.
My honest verdict: this is one of the most useful founder stories available because Nathan documented everything publicly in real time — including the failures. ConvertKit publicly shares their revenue, churn numbers, and more at convertkit.baremetrics.com. That transparency is itself a lesson. Founders who hide their numbers never build the kind of trust that drives word-of-mouth growth. The five decisions matter. The transparency habit that ran underneath all of them may matter more.
Key Takeaways
- Advisor advice is based on visible data — only the founder knows what hasn't been tried yet.
- Splitting attention between a working business and a struggling one guarantees both underperform.
- A niche too small for VC is not a niche too small for a real business — it's a wedge.
- Unscalable work in the early stage is not inefficiency — it's the fastest feedback loop available.
- Removing the biggest barrier to trying your product matters more than almost everything else early on.
- Public transparency about revenue and failures is itself a growth strategy — not just a personality trait.
Frequently Asked Questions
More Founder Stories Worth Reading:
- He Intentionally Lost Half His Revenue Overnight — and It Saved His $5M 3D Printing Business — Another founder who made a decision every advisor said was wrong
- He Built a $17K/Month App in 10 Hours a Week — With Zero Ad Spend — The YouTube distribution playbook ConvertKit's Pat Flynn webinar used in a different form
- 6 Boring Businesses That Keep Making Millionaires — ConvertKit started as a "boring" email tool for a niche — same pattern, different industry
Sources referenced in this article:
- Nathan Barry — Growing ConvertKit to $5,020 MRR (original post)
- ConvertKit public revenue dashboard — Baremetrics
- StartupGTM — ConvertKit Growth Story
What This Story Doesn't Tell You
The five decisions in this article are real, documented, and worth studying. But there's a version of this story that gets told without the context that makes it honest: Nathan Barry was not an unknown founder building in the dark. He had an existing audience of tens of thousands of people, a reputation in the creator economy, and $250,000 a year in other income that funded the years when ConvertKit generated almost nothing.
The decisions are transferable. The starting position is not. Most founders applying these lessons will be doing it without Nathan's distribution advantage — and that changes the timeline, the required capital, and the risk profile significantly. Apply the playbook. Be honest about what you're starting with. Those are two different things, and conflating them is the mistake most startup advice makes.