A bootstrapper publicly commits to $5,000 a month in six months, misses badly, and eighteen months later is told to shut it down.
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Nathan Barry was doing well by most measures. He was a designer who had figured out how to sell information products: The App Design Handbook made $12,000 on launch day, and his books and courses would eventually generate around $250,000 a year.
The problem was structural rather than financial. Every launch was a spike followed by a decline, and every month started at zero again. He wanted recurring revenue — income that did not require him to manufacture a new event every quarter. That desire, plus a specific irritation with the email tools available to writers like him, set up what came next.
On January 1, 2013, Barry announced the Web App Challenge in public: he would build a software business to $5,000 in monthly recurring revenue within six months, investing $5,000 of his own money and roughly 20 hours a week. He committed to posting the numbers either way.
The idea he landed on within the first week was ConvertKit — email marketing built specifically for bloggers and authors rather than for every small business on earth.
What makes this a real tipping point is that the public commitment was the mechanism, not the marketing. He wrote at the time that complete failure was unlikely but partial failure was probable, and that if he failed it would at least be in the open. He did fail: at the six-month mark ConvertKit was at roughly $2,480 in monthly recurring revenue, about half the target.
Then it got worse. Growth stalled, and by October 2014 — twenty-two months in — monthly recurring revenue had slid to $1,207. Part of the cause was a targeting mistake: he had aimed education at beginners building their first list, who complained about price and cancelled when their projects died, while experienced creators with large lists were put off by the beginner positioning.
A respected advisor told him to shut it down. Barry had three options: kill it, coast on autopilot, or commit.
He committed, in the most expensive way available. He shut down his profitable $250,000-a-year course business entirely, injected $50,000 of personal savings, hired a full-time developer, and started emailing bloggers one at a time — offering to migrate their lists, tags, and automations for them, free.
The curve broke almost immediately after the decision. Monthly recurring revenue rose 23% in one month, then 27% the next. By March 2015 it was around $5,020 — the original target, twenty-six months late. June: $10,000. December: $97,000. By the end of 2016: $625,000 a month.
The engines were unglamorous and repeatable: free concierge migrations that removed the switching cost, affiliate partnerships paying recurring commissions to creators, and heavy investment in webinars and education rather than advertising.
Kit today reports over $43 million in annual recurring revenue, has never raised outside funding, and has been profitable every year. Barry turned down an acquisition offer from Spotify reportedly in the hundreds of millions in 2021.
Two lessons here run against common advice.
The first is that killing profitable revenue can be the growth move. Barry's course business was working — that is exactly why it was dangerous. It absorbed the attention the compounding business needed, and the sensible-sounding plan of running both would have kept ConvertKit near zero indefinitely. Choosing focus meant destroying income, on purpose, at the moment things looked worst.
The second is that his public failure became his distribution. Building in the open through a challenge he visibly missed created an audience invested in the outcome. Most people would treat missing a public target as humiliation; it functioned as marketing.
Worth noting: the revenue figures throughout are self-published rather than audited.
The framework: build in public, then kill your profitable side income to force focus onto the compounding one.
Move 1 — Set a specific public target with a deadline and a dollar figure, and commit to publishing the numbers monthly whether they are good or not. The accountability is the point; the audience it builds is the bonus.
Move 2 — Pick the narrowest possible customer and check you are targeting the experienced end of that niche, not the beginner end. Beginners churn, complain about price, and repel the customers who would actually pay.
Move 3 — Remove the switching cost by hand. Barry's team migrated lists, tags, and automations for free, one customer at a time. Whatever makes leaving a competitor painful, do that work yourself until you can afford to automate it.
Budget line: $5k to start and roughly 20 hours a week — but the real number is the 22 months of near-zero revenue before the inflection, and the profitable income you may have to cut to get there.
Revenue figures are self-published rather than audited.
Last verified 2026-09-01
Same structure every time — the tipping point, the first ninety days, and a playbook with real numbers attached.