Kit (formerly ConvertKit): the near-failure that a public teardown saved

The original problem. Professional bloggers and course creators needed email marketing built around people rather than lists — tagging, automation, and selling — and the available tools (Mailchimp, AWeber) were built for a different job.

Founder background. Nathan Barry was a designer who had self-published books about design and made good money doing it. He had a specific and unusual asset: he was a member of the exact community he intended to sell to, and he had already built an email list of them.

Initial product and near-death. Barry launched ConvertKit in 2013 as a "$5,000 product challenge." After roughly 18 months it was at about $1,300 in monthly recurring revenue and he was close to shutting it down (Nathan Barry, "Growing ConvertKit to $30,000 in Monthly Recurring Revenue") [Founder's own contemporaneous account]. Ten thousand dollars a month of his own book income was subsidizing it.

The turning point — and what actually caused it. Barry did three things in 2014–2015, and the founder-told story tends to credit them jointly:

1. He stopped treating it as a side project and committed full-time, hiring a direct-outreach marketer.
2. He ran concierge migrations — ConvertKit staff manually moved a prospect's list, forms and sequences off Mailchimp for free. This removed the single largest switching cost in email marketing, and it is the most transferable tactic in this case.
3. He started publishing monthly revenue reports publicly, which turned the company's growth into content that his target audience — creators who love business transparency — actively followed and shared.

The company went from ~$1,300 MRR to over $100,000 MRR in roughly two years, and to $36M+ ARR by around 2022 [Reported, from Barry's published reports; the company stopped publishing detailed monthly numbers later].

Concrete mistakes. Barry has been explicit that the first eighteen months were wasted on building features instead of talking to customers, and that he priced too low initially. He has also said publicly that he underestimated how much of the early growth came from his existing audience rather than from the product — an unusually honest admission for the genre.

Current status (September 2026). Rebranded from ConvertKit to Kit in 2024. Self-funded. Serving 550,000+ creators, with a creator network/sponsorship marketplace, three physical "Kit Studios" (Boise, Chicago, and a new NYC location opened in 2026), and an annual conference, Craft + Commerce (Tubefilter, July 2026). Barry's stated position: "We don't have growth targets to hit." The company does not publish current ARR.

Lessons that generalize.

1. Removing switching cost beats adding features. Concierge migration was expensive per customer and unscalable — and it was the right thing to do at that stage, because it directly attacked the reason prospects said no.
2. Public transparency is a distribution channel only for audiences that value it. It worked for Kit and Buffer because their customers are creators and marketers who find business metrics inherently interesting. Publishing your MRR to a hospital procurement department accomplishes nothing.

---