How Nathan Barry bootstrapped ConvertKit to a $30 million company.
A deep dive into how Convertkit went from zero to being a $30 million company while being bootstrapped.
Friends,
Today, ConvertKit is a thriving company valued at over $100 million, serving more than 30,000 creators who use the platform to grow their audiences and build their businesses. But the path to success was anything but smooth.
ConvertKit was bootstrapped by Nathan Barry in 2013 when he set out to create a SaaS product that would generate recurring revenue. At the time, Nathan was a successful ebook author who had made $85K in just four months.
Nathan soon realized that relying on one-time sales was unsustainable. This led him to launch "The Web App Challenge," an ambitious project to build a software product that could earn $5,000 in monthly recurring revenue (MRR) within six months.
However, the journey was far from easy. Growth stalled, and at one point, revenue declined to as low as $1,207 per month. It was a tough road, but Nathan didn’t give up.
Through relentless focus, strategic pivots, and a deep understanding of his target audience, Nathan turned ConvertKit into a powerhouse in the email marketing space.
This is the story of how ConvertKit evolved from a modest side project into a leading platform for creators worldwide, achieving extraordinary growth and success against the odds.
Let’s dive in, shall we?
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How Nathan Barry came up with the idea of ConvertKit
In 2012, Nathan Barry made $85K in just 4 months selling ebooks. But despite the success, he saw a major flaw—his income relied on one-time sales, creating unpredictable cash flow and constant pressure to keep selling.
So, Nathan shifted gears to build a software product that would generate recurring revenue. On Dec 31, 2012, he announced "The Web App Challenge"—a 6-month goal to build a web app generating $5K MRR. The catch? No idea, $5K budget, and only 20 hours/week to work on it.
He started by focusing on finding a painful problem to solve—one that people would pay to eliminate. The plan? Talk to potential customers, discover their pain points, validate them with others in the industry, and gauge how much they’d pay for a solution. Nathan reached out to his network—lawyers, insurance agents, real estate pros, and more—to uncover a common pain point.
The process wasn’t easy. Many people he spoke with shared software ideas, but none were worth pursuing. Nathan learned that uncovering real pain points required deep conversations—people often glossed over their frustrations to pitch ideas instead.
At this time, Nathan received crucial advice from his mentor, Amy Hoy: “Building and marketing software is hard. Don’t throw away all your competitive advantages to make it even harder.” She urged him to focus on what he knew best, leading Nathan to rethink his approach.
Nathan realized his competitive advantage was his experience as a creator. He knew the frustrations of managing email lists, drip-feeding content, and launching products. Instead of solving problems in unfamiliar industries, he decided to build a tool that solved his own problem—better email marketing for creators like him.
This decision marked the start of ConvertKit—a platform designed by a creator, for creators. Born out of real frustration and validated through real conversations, ConvertKit turned into a beloved tool for thousands of online creators worldwide.
How Nathan validated ConvertKit
Nathan DM’d people on Twitter, asking if they had 15 minutes to hear his product idea. Most agreed, and 8 out of 10 said “Yes!” when asked, “Is this something you’d buy?” So the idea was validated, right? Well…
People often say they’d buy something during market research, but they rarely follow through when it’s time to pay. With info products, pre-orders solve this issue. He sold 3-month licenses and gave another month away for free.
He wrote and launched a ConvertKit sales page with 3 price tiers:
Beginner $112 (3 months at $37/month)
Intermediate $281 (3 months at $93/month)
Expert $562 (3 months at $167/month)
Nathan tweeted the sales page link and emailed his subscribers. Soon, pre-orders started rolling in—19 in total, adding $2,916 to the budget and $972/month in revenue. The idea was validated, but ironically, none of the pre-orders came from those who said they’d buy!
The lesson? it doesn’t count as validation until your customers have paid you money.
Stalled Growth & Pivot
Once ConvertKit was up and running, Nathan realized just how tough it was to generate significant revenue with a SaaS business. So, in January 2014, he tried a different approach—selling ConvertKit as an info product by launching ConvertKit Academy.
Nathan launched ConvertKit Academy monthly, accepting just 10 people at $300 each. They’d get a 6-month membership, an email marketing course, templates, and hands-on help with setting up accounts, embedding opt-in forms, and crafting marketing strategies.
This approach gave Nathan the best of both worlds—he could build anticipation, launch, and make a decent chunk of money in 1 day while boosting MRR. But while ConvertKit Academy reduced churn and solved cash flow issues, it also attracted the wrong type of customers.
Focusing on education—especially building a list from scratch—attracted beginners who weren’t the best customers. They often complained about price, struggled with consistency, and canceled when their projects failed. Worse, experienced creators with big email lists were put off by ConvertKit’s focus on beginners. “We were driving away our best customers and focusing on those least likely to succeed.”
So in June 2014, Nathan stopped promoting ConvertKit Academy. Growth stalled. And by October 2014, ConvertKit revenue had dropped down to $1207/month, and Nathan realized that something had to change.
Doubling down on ConvertKit - Road to $5k MRR
Nathan had three options: shut down ConvertKit, put it on auto-pilot, or double down and give it the time and energy it deserved. Shutting down wasn’t an option—it was too powerful a tool. He could’ve let it coast, but instead, he chose to go all in and see if ConvertKit could truly succeed.
But first he had to answer: Who was Convertkit for?
That was a question that he never had a really good answer for. The answer was something like, “anyone trying to build an audience quickly and sell products online.” That’s not good. He needed to be specific.
ConvertKit’s messaging wasn’t tailored to a specific market, so no one felt it was made just for them. Nathan decided to focus on one market and align all messaging to match. While still welcoming others, this gave ConvertKit a clear, focused audience to pursue.
Nathan chose to focus on email marketing for authors. He noticed that many of his most successful customers were writing and selling books or courses—just like him. ConvertKit was built with this exact use-case in mind, making it the perfect tool to sell more books and courses.
This new focus, combined with full-time work on ConvertKit, reversed the revenue decline. By the end of October, MRR grew 23% to $1,646. November saw another 27% increase, reaching $2,100.
And it soon reached $5k MRR. Things were finally looking up!
How Nathan used outbound emails to get to $98k MRR
Around this time, Nathan also began doing direct sales. Previously, if someone expressed interest at a conference, he’d chat and try to remember to follow up later. Now, he started tracking every conversation in a Trello board, ensuring no leads slipped through the cracks.
Focusing on authors allowed Nathan to start reaching out to potential customers. He emailed top sellers on LeanPub and Udemy—out of about 100 personal emails, he landed 5-7 new customers. Not bad for the early stage.
When Nathan tried raising capital, VCs said the market was too narrow. So, he niched down even further: “email marketing for professional paleo recipe bloggers who are women” or “Men’s fashion bloggers in NYC.” This strategy let him compile targeted lists using Twitter, Google, & top blog posts. He subscribed to their newsletters, followed them on Twitter, & engaged with their content so they’d recognize him when he reached out.
Nathan’s email strategy was simple: he’d ask about frustrations. Instead of pitching ConvertKit, he asked what was frustrating them about MailChimp, Aweber, or whatever they were using. The emails were short, personal, and name-dropped relevant customers.
The responses poured in. Bloggers were frustrated by their tools’ limitations—no list segmentation, opt-ins, or automated email courses. The same frustrations that led Nathan to create ConvertKit. This naturally led to conversations about how he’d solved those issues. He offered calls to give tips on improving their current setup & show what ConvertKit could do. Nathan did 100s of Skype calls.
Most early sales conversations ended with, “ConvertKit sounds great, but switching providers is too much work.” Nathan tried everything: “It’s not that hard” or “you just have to...” but nothing worked. Out of desperation, he offered, “I’ll do it for you for free.” It worked! That’s how the concierge migrations program was born. Nathan would manually move everything—forms, sequences, templates—for free, even for a $50/mo customer. Tedious, but effective.
Once a customer was set up and successful, Nathan would ask, “Who else should I talk to?” They’d always have a few bloggers to suggest. These warm intros worked far better than cold outreach. Soon, referrals were driving as many calls as cold emails. Influential bloggers like Pat Flynn and Wellness Mama switched, then started hinting about the new tool they were using.
When following up, Nathan would say, “I'll follow up once more in 2 weeks. If I don't hear from you, I’ll assume it’s not a good fit.” But he’d still engage with their content. Many came back later when the timing was better.
Nathan also noticed a problem with the “Email marketing for authors” focus. Customers who identified as "authors" were often hobbyists with small accounts, needing the most help and most likely to cancel. The best customers weren’t starting from scratch—they were switching from another provider. These customers didn’t see themselves as just authors; they were bloggers, course creators, and more.
During this time, ConvertKit made big moves:
David revamped marketing automation, enabling fully automated sales funnels.
They rebranded as “Email marketing for Professional Bloggers” to reflect their best customers.
Focused on direct sales, targeting pro bloggers with 30K-250K subscribers.
Provided top-notch support and concierge migrations to help these bloggers grow faster.
Highlighted their favorite customers’ success stories.
By July 2015, ConvertKit’s MRR soared from $1.5K to $15K.
Nathan also rolled out an affiliate program to reward early promoters and started hosting group demos and webinars to handle the influx of leads. By year-end, ConvertKit hit $98K MRR. The momentum from incredibly unscalable work had turned into scalable growth.
How ConvertKit used webinars to scale to $900k MRR
Since ConvertKit was bootstrapped, they had to rely on low-cost strategies. They couldn’t afford big ad spends like other companies, but they had time.
Their marketing strategy focused on content marketing, direct sales, and most importantly, webinars.
Webinars were cheap to run and naturally built a community around their new product. More importantly, they consistently generated new signups. The goal? Book as many webinars as possible—no limits.
And that’s exactly what they did.
ConvertKit gave the same webinar over and over, but with different partners, mostly from their affiliate program. They did 20-30 webinars a month, sometimes 2-3 a day. It was exhausting, but it worked.
The result? A 637% growth in monthly revenue.
The first key to ConvertKit’s successful webinar strategy was their wide-open affiliate program. Anyone could become an affiliate—no application needed. Affiliates earned a recurring 30% commission for the life of each customer.
This created loyalty and fueled growth.
At one point, ConvertKit had 13,000 customers and 4,000 affiliates. It was part of the new customer drip—everyone who signed up got a chance to be an affiliate.
They’d do a webinar with any affiliate, no matter how small their audience.
One big win was a webinar with Pat Flynn. Within 24 hours, thousands signed up for ConvertKit. The success of big webinars like Pat’s helped ConvertKit capture the interest of other influential bloggers.
In these webinars, ConvertKit gave away online courses, ebooks, and t-shirts. Partners often had their own freebies too, like an online course on how to optimize ConvertKit.
One partner showed how to use ConvertKit from her own account, boosting her leads significantly. Participants got a free month of ConvertKit, courses, and valuable info on how to get the most out of it.
This built trust and goodwill from the start. Even if participants didn’t use the free month, they were now leads in ConvertKit’s sales funnel. Their first experience was getting $400 worth of free stuff and a no-strings-attached trial. This kept them excited and open to the brand.
It’s important to note: Courses and webinars work best with a narrow, targeted audience. They’re not for everyone.
One reason for ConvertKit’s success was that it was a service created by bloggers, for bloggers.
ConvertKit kept the technology simple. At first, they used Leadpages, YouTube Live, and Chatroll—all put together on one page, streaming live through Google Hangouts.
About six months in, they switched to a custom WordPress page, but kept YouTube and Chatroll.
Promo links were managed through an affiliate program called Ambassador. The most complex data they tracked were affiliate signups, which they used to run follow-up webinars for partners with a lot of signups.
For webinars, they tracked only essential data—attendees & signups.
8 key takeaways from ConvertKit
Identify your competitive advantage: This is your moat.
Persistence Pays Off: Stick with your vision, even when growth stalls.
Listen to Your Customers: Build products that solve real problems for your audience.
Make Bold Decisions: Don’t be afraid to pivot and double down when necessary.
Embrace an Audience-First Approach: Focus on creating value for your users to build a loyal community.
Validate Your Ideas: Test your concepts with real customers before scaling. Remember payment is the ultimate validator.
Adapt to Market Needs: Continuously refine your product to stay relevant.
Solve Specific Problems: Dedication to solving a clear problem can drive extraordinary growth, even in competitive markets.
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