Taking a Side Hustle from $0 to $18 Million in Revenue with Nathan Barry

Posted on November 12, 2019

How does a company end up with hockey stick growth?

ConvertKit went from $1300 to $100k in MRR in 12 months, and are now doing upwards of $18 million in revenue.

The craziest thing, ConvertKit, started as a side project and had begun to lose momentum before Nathan decided to redouble his efforts in trying to grow it. Twelve months later, he was doing $100k in MRR.

So, what happened? We cover:

– How Concierge Migrations helped Nathan Barry acquire customers from MailChimp, and accelerate their growth from $1300 to $100k in MRR.

– What other growth channels ConvertKit added to help them scale their user acquisition.

– How ConvertKit split their onboarding flow by a series of questions to make it more contextual to different user segments.

Happy Growing!


Time Stamped Notes

[4:10] – ConvertKit was the result of Nathan undertaking the ‘Web App Challenge.’ He publically committed to creating a product that generated $5k in MRR within six months.

After six months, ConvertKit was generating $2k in MRR. Nathan began to lose momentum with the product and didn’t start to redouble his efforts until 18 months later.

[6:40] – Nathan developed ConvertKit to solve the problems he had as a blogger.

[9:30] – A significant shift in ConvertKit’s success was when Nathan took on a technical co-founder who could take ownership of the product development.

[12:35] – Once Nathan’s co-founder joined, he began to double down on customer acquisition. Something that worked great was ‘concierge migrations.’ Nathan would log in to a potential customer site and copy everything from their MailChimp app to ConvertKit, so they could see/experience the value of the app.

[14:25] – Concierge migrations were a big part of how ConvertKit went from $1300 to $100k MRR in 12 months. By doing direct calls with potential customers, Nathan got real feedback on the reasons people were hesitant to signup.

The number one piece of feedback was the hassle of switching, so Nathan offered doing the migrations for free expedited their results.

[19:20] – The ConvertKit team started to automate a bunch of that migration from MailChimp. They’re still doing 10 to 15 migrations per week.

[21:45] – ConvertKit’s affiliate program was a big part of how they went from $40k to $100k in MRR. There were some significant influencers in the blogging space that had large audiences they could promote ConvertKit to.

[26:00] – ConvertKit is getting 6,000 to 7,000 trials a month. One of their goals is to improve the free to the paid conversion rate of their free trials. They split their onboarding flow by the platform you’re switching from and the number of contacts you’re bringing over. Doing that helps to make the experience more contextual for the user.

[29:20] – Some of the things Nathan is focusing on to keep accelerating growth are – improving activation, product virality, incentivized virality, and growing communities.

[33:15] – ConvertKit is a remote-first company. Nathan feels that’s a huge benefit in both hiring from anywhere, and retaining those people.


– Nathan on Twitter / LinkedIn
– Kieran on Twitter / LinkedIn / Medium
– Scott on Twitter / Linked / Medium