Quick Win: ConvertKit's Nathan Barry on how flywheels transformed his business
6 Apr 2026 · 3 min
Nathan Barry, ConvertKit's founder, explains how he applied physics' flywheel concept to grow his business. He built a direct-sales loop: targeted prospecting, personal calls to find pain points, a concierge migration service, then testimonials that brought referrals. Each piece fed the next, compounding momentum.
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In the world of business and startups, how do you turn hard manual effort into effortless momentum? Nathan Barry, the founder and CEO of ConvertKit, has found a way, and it all comes down to a concept from physics called a flywheel. So what on earth is a flywheel, and how did Nathan use the concept to revolutionize ConvertKit's sales process and turbocharge his company's growth? Welcome to How I Work, a show about habits, rituals, and strategies for optimizing your day. I'm your host, Dr. Amanda Imber. On today's quick win episode, we go back to an interview from the past and I pick out a quick win that you can apply today. In today's show, I speak with Nathan Barry about how he applied flywheels Grow Convert Kit.
Yeah, so a flywheel is a concept in physics really of taking manual effort and then transferring it into something that like either storing the energy or carrying it forward. So the first time that I encountered a flywheel was in 2008, and I was in Lesotho, which is a landlocked country inside of South Africa, and we were working at an orphanage and we had drilled a well and we were going to put a pump on top of of the well. And Maseru, the capital city where we were at, had electricity, but in the 2 weeks we were there, I think it went out like 8 times. So we didn't really want to put in an electric pump on this well. And so I was thinking like, okay, we're adding a hand pump. And Jason, one of the guys leading our trip, was like, no, no, no, we're going to put a flywheel on it. So instead of the hand pump, which would be this long handle, you go and pump your water, and this handle gives you leverage, but there's a direct tie between the effort that you put in and the impact or the results that you get back. And the moment you stop pumping, you immediately stop getting water. And so instead of that, the flywheel is this large metal wheel that sits up on top of the, the pump. It's hard to get going initially, but instead of this linear up and down movement, it carries that momentum forward and it builds momentum over time. It still needed input, but I could basically with one or two fingers just keep this thing spinning. And so That's a metaphor, obviously. Like, we get to apply it to all these other areas of life and business. And like we talked about health and fitness, that's a flywheel. It is incredibly difficult to get going if you're starting with really small changes. You're just saying, oh, I'm going to eat a piece of fruit every day. You can build on from there. So I really came to 3 laws that define a flywheel, especially in the business case. The first is every step in a flywheel should flow smoothly from one into the next. The second law is that it should get easier with each rotation. And then the third law is it should deliver more with every rotation. So that's flywheels at a high level, but, and we can go wherever you'd like from there.
I would love to get an example from within ConvertKit in the sales process, because I think everyone listening will have some kind of a sales process in their business. Maybe they are directly involved in sales. How have you gone about applying the flywheel concept to driving sales at ConvertKit?
One of the biggest things that I did is I started direct sales. Being a content marketer, I was thinking I'm going to grow through content, right? That is how this business is going to grow. Turns out it's really, really hard to sell software through content, especially software that's not very good yet because it's new. And so the pivot to direct sales really let me grow the company and get traction early on, especially 'cause what happens when selling through content is If you and I are having a conversation, we're sitting across from each other at a coffee shop, and I'm saying, "Would you like to buy ConvertKit, become a customer?" If you were to like look at me and then like push back your chair and without saying anything, just get up and leave, that would be socially unacceptable on so many levels, right? If I say, "Hey, will you buy this thing?" You are obligated by the rules of our society to give me a response. It might be like, "Maybe I'll think about it," or "No," but you have to give me a response. And whatever response you give me, I can learn from that. But when you think about content marketing, that socially unacceptable interaction happens all the time. I can just hit the back button. I have completely rejected you. You get no feedback. And that's what happens on the web. So I love it when people will go into direct sales because it gets them all of this feedback. So my flywheel for ConvertKit direct sales, like it worked. And then now years later, I'm like, why did that work? I'm like, that was a flywheel and I didn't even realize it. So I started just identifying potential customers. I looked at who was successful on ConvertKit and I was like, okay, let me find people like them. That got me like lists of men's fashion bloggers in New York, paleo recipe blogs, try to get as specific as possible. Then I'd reach out with a personal message and I would ask about what was frustrating. So specifically I'd see they're using Mailchimp and I'd say, hey, I was wondering what's your biggest frustration with using Mailchimp? The reason I ask is I'm working on building a tool called ConvertKit and it's used by and I would drop my, the only two relevant names that I had that was a customer or someone else. And I just love to get your feedback, right? So I'd start with that. It had a pretty good reply rate. People would say, oh, I'm really frustrated with, it's hard to tag and organize my audience. It's hard to set up automations that are relevant to my subscribers, things like that. Which very conveniently I built the product because I used Mailchimp and I was frustrated by these exact same things. And so I'd say like, oh, Here's how we're solving it. I'd love to get on a call and show that to you. And that worked really well. And at some point I'd ask for the sale and they would usually say no. Now thankfully, because we're on a call, they had to tell me why. And the reason they said why was usually it's too much work to migrate. We've been using this other tool for 3 years, 5 years, and we're deeply embedded until finally, like out of desperation, I'm like, it's not that much work, blah, blah, blah. I'll do it for you for free. And that's where our concierge migration was born. And I would pull up their Mailchimp account and their ConvertKit account here and I'd like copy and paste over their emails and then edit all their forms and switch those over. And what that did is that's how I landed the customer. And then I would get a testimonial and the recommendation, hey, who else should I get on ConvertKit? That recommendation to other people completed the loop, right? It brings my flywheel background to the beginning because then now I've identified new customers. And so if we go through our 3 laws for this direct sales flywheel, first is every step moves smoothly one into the next, right? Migration goes to testimonial, which leads to new customers or new referrals that I can then talk to. Next, it gets easier with every rotation because my prospecting got more dialed in. My cold email, I knew what worked. My sales calls got a lot better. The product got better. And then it also drove more results with every rotation because I could reach more and more people. Word of mouth started to kick in a little bit. And so I just noticed that that flywheel was so hard to turn at first, but it got just a tiny bit easier with every rotation up until the point that we just had a huge amount of momentum and word of mouth.
That's such a great story, such a great example. I love that. I hope you enjoyed today's Quick Win episode. If you would like to hear the full chat with Nathan Barry, you can find a link to that in the show notes. If you're looking for more tips to improve the way you work and live, I write a short weekly newsletter that contains tactics I've discovered that have helped me personally. You can sign up for that at amantha.com. That's amantha.com. If you like today's show, make sure you hit follow on your podcast app to be alerted when new episodes drop. How I Work was recorded on the traditional land of the Wurundjeri people, part of the Kulin Nation. A big thank you to my editor Rowena Murray and Martin Imber for doing the sound mix.
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