Nathan Barry: From Near-Shutdown Side Project to $45M+ ARR with Kit
How a designer and author turned a stalled email tool into the bootstrapped operating system for creators after a blunt advisor conversation and unscalable migrations.
- MRR
- ~$3.75M (derived)
- ARR
- $45M+
- Users
- 50,000+ creators
- Founded
- 2013
- Team
- 95+
- Stack
- Ruby on Rails, AWS, Stripe
How did Kit start?
I started as a designer and writer. I published books and courses on app design and audience building, built an email list of tens of thousands, and ran a profitable info-product business. The email tools available felt wrong for creators like me. Mailchimp and similar platforms were either too basic or built for enterprise marketing teams with different workflows. I wanted something that handled deliverability for content emails, tagging by interest, and the practical needs of people selling courses, books, and newsletters.
On January 1, 2013 I publicly announced a Web App Challenge: build a SaaS to $5,000 in monthly recurring revenue in six months while spending no more than $5,000 of my own money. The product was ConvertKit, focused on professional bloggers and creators. Early traction appeared, but the product stayed rough and my attention stayed split with the book business. By the end of the challenge period we were around $2,000 MRR. Over the next year revenue drifted lower.
What almost killed it?
By late 2014 ConvertKit was stuck near $1,200–$1,500 MRR and slowly declining. The open metrics on Baremetrics showed the flat or downward line clearly. I was treating it as a side project while the books and courses paid the bills. At a conference I sat down with Hiten Shah. He told me the honest version: either shut it down and move on, or stop treating it like a hobby. Put real money and full-time attention behind it, or admit the experiment had failed.
I went home and chose to double down. I shut down the other products that were competing for time, cashed out investment accounts, and put roughly $50,000 of personal savings into the business. That funded a small team, including a full-time Rails engineer, and gave a short runway. The decision was not heroic in the moment; it was the only way to stop wondering whether the product could have worked if it had ever received a real chance.
How did the unscalable work create scale?
Switching email tools is painful. Lists, automations, and history do not move cleanly. I started offering free concierge migrations. I (and later the team) would personally move a creator’s list and sequences so the switch cost them almost nothing. Cold emails and direct outreach to professional bloggers turned into calls, then into hand-held migrations. Most of those customers stayed. The early work did not scale, but it produced the retention and word-of-mouth that later channels needed.
From there we layered an affiliate program with a meaningful recurring commission. Creators who already recommended tools to their audiences had a reason to talk about ConvertKit. The combination of high-touch onboarding, a narrow focus on professional creators rather than every small business, and public metrics created a flywheel. Public posts about the numbers and the process also attracted people who wanted to see a bootstrapped path that was not purely solo-indie micro-SaaS.
What does the business look like now?
ConvertKit rebranded to Kit in 2024 to reflect a broader set of tools for creators who treat their audience as a business. The product now covers email, automations, recommendations, commerce features, and related workflows. On my personal site I list $45M+ in annual recurring revenue, more than $5M in annual profit, a team of 95+ people across roughly 70 cities, and more than 50,000 creators using the platform. These are self-reported figures. Earlier public milestones include crossing $1M MRR in March 2018 (announced on X) and sustained growth that put the company on the Inc. 5000 list multiple times while remaining fully bootstrapped.
We have shared millions in profits with the team. Transparency around metrics was a deliberate choice for years via the Baremetrics open dashboard; it forced clearer conversations internally and externally. The core stack has stayed practical: Ruby on Rails for the application, AWS for infrastructure, Stripe for billing, and dedicated email-sending infrastructure focused on deliverability. Growth has come from product improvements that reduce churn, the affiliate and partner channel, and continuing to serve creators who already pay for tools that help them earn.
Lessons that still feel true
Give the project a real chance or shut it down. Treating something as a side experiment for years can look like persistence while actually preventing the conditions needed for success. The $50k and full-time focus were not optional once the choice was made.
Do the work that does not scale first. Concierge migrations were slow and manual. They also created customers who stayed and referred others. Once those customers existed, more scalable channels (affiliates, content, product-led expansion) had something to compound.
Narrow the customer. Competing broadly with Mailchimp on price or features was a losing path. Serving professional creators who needed specific deliverability, tagging, and monetization workflows produced higher willingness to pay and better retention.
Public metrics create accountability. Seeing the flat line on a public dashboard made the problem harder to ignore. It also attracted people who valued the same approach. Not every company needs full transparency, but the discipline of knowing the numbers in detail is non-negotiable.
Finally, the rebrand and product expansion happened after the core email business was durable. Expanding too early would have diluted focus while the business was still fragile. The current scale is the result of surviving the early plateau long enough for compounding to matter.
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