Using ConvertKit to Drive Business

How I Built It
How I Built It
Using ConvertKit to Drive Business

Sponsored by:

TextExpander logo
FreshBooks cloud accounting

Last week, you heard from Angel Marie about the importance of building your list, and how you can use ConvertKit to do it. Today, I decided to pull back the curtain and tell you exactly how I use ConvertKit.

Show Notes


Hey everybody and welcome to episode 158 of How I Built It, the podcast that asks, “How did you build that?” Last week, we heard from Angel Marie about the importance of building your email list – and a sweet deal to go along with it!

Today I want to share with you how I’m using ConvertKit in my own business. We’ll go over why I choose ConvertKit, how I’m using it to get subscribers, and how I’m automating messages and delivering relevant emails based on how I have them organized…but first, a word from out sponsors.

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If you want to check out what YITH can do for you, you can check them out at And exclusively for How I Built It, listeners, you can get 10% off your purchase with the code BUILDIT. That's and the code BUILDIT at check out.

Switching from Mailchimp

I wasn’t always on ConvertKit – for most of my career I used Mailchimp. It was free for the number of subscribers I had, and I was able to do just want I needed to: send email to those people. Subscribers are organized by list and when I used it, I don’t think there was a way to automate and segment outside of that.

When I attended CaboPress, a conference for people who want to grow their business, in 2017, that was the first thing I changed. After hearing my friend (and friend of the show) Chris Lema talking about making sure your website visitors and customers are in the right “swim lanes,” I realized I knew nothing about my customers. So that day I signed up for ConvertKit.

Tagging Subscribers

The main reason I wanted to get into a more robust system like ConvertKit was so that I could tag my subscribers – basically assign them labels based on their interests and reasons they signed up.

At the time I was kind of all over the place with my offerings. I was doing dev-centric stuff, content for site builders, and general freelancer content. I just didn’t know what was working, or how my messaging was landing.

(Over time, I would learn that I didn’t have very good messaging in general)

With ConvertKit, I could tag users based on the form where they signed up, as well as a whole host of other information, including:

  • Courses they bought
  • Links the clicked on
  • Questions they asked or answered

This helped give me fantastic insight into who was on my list, and what they wanted to learn.

For a while after this I was a little drunk with power. I was tagging users based on every little thing they did, regardless of if it I was using it or not. Maybe, just maybe I would want to know this in the future. I still didn’t know what I was trying to offer, as it turned on. Of-course, I’ve fixed that, and now I have a much clearer method for using ConvertKit, which I’ll tell you about after the break.

This episode is brought to you by TextExpander. Save time typing and boost your productivity with TextExpander. You know I’m all about automation, and TextExpander is a great way to get started. It allows you to create your own snippets for repetitive text you tend to use everywhere. Add the text, create a snippet, and boom.  One of my favorites is my address. Instead of typing out my full address and risk typos, I simply type $-a-d-d-r and let TextExpander do the rest. This is all without special app-specific plugins. Do it anywhere you type. 

But that’s not all it does. With its advanced snippets you can create fill-ins, popup fields, and more. You can even use Javascript or AppleScript. Another one of my favorite (and most used) snippets is p-p-t. It will take whatever text I have on my clipboard, and convert it to plain text. No more fighting formatting! 

Plus, if you work with employees or contractors, you can use TextExpander  to manage and share snippets with them, so you all get it right, every time..

They also host interesting webinars every month, like Power Tools for Customer Support Professionals with HelpScout in March. 

TextExpander is available on macOS, Windows, Chrome, iPhone, and iPad. If you’ve been curious about trying TextExpander or simple automation in general, now’s the time. Listeners can get 20% off their first year. Just visit and let them know I sent you. 

How I’m Using ConvertKit Today

Today I have 2 “buckets” for my subscribers: Freelancers who want to become more efficient (and therefore, more profitable), and hopefully podcasters trying to launch/sustain their own shows.

Lead Magnets

My strategy for connecting with these folks is pretty simple (though I’ll likely continue to evolve it). I have 2 lead magnets. For the freelancers, a PDF that outlines 5 Tools to help you build websites faster, and for podcasters, the podcast workbook – a guide to help you launch your show, with prompts and checklists.

The 5 Tools PDF is a great introduction to what I’m offering as courses through my membership. By the end of 2020, I should have courses on how to use each of those tools – so if the subscriber is interested in learning how to use the tools, and not just what they are, they can.

The same thing goes with the podcast workbook. It focuses on what they need to do, but not exactly how to do it. This is hugely helpful for people who need to get started. Then my Podcast Liftoff course will should them how to do everything, if they need it.


Once they sign up, they’re automatically tagged and put into a sequence. This is where ConvertKit is really powerful. The automations allow you to tag and add to mailing sequences based on specific actions (like signing up on a specific form).

The sequences are a set of emails that go out automatically on whatever schedule you’d like. So in both cases, subscribers get added to an appropriate 5 email daily (on weekdays) sequence with questions and helpful information. At the end of the sequence, I make a soft sell, then add them to one of 2 “regular” (weekly) lists: one for general freelancers, and one for podcasters.

This helps me deliver helpful, relevant content. And this is important! We’ll get into why, but first, a word from FreshBooks.

Do you remember when you started your small business? It was no small feat. It took a lot of late nights, early mornings, and the occasional all-nighter. Bottom line: you’ve been insanely busy ever since.

So why not make things a little easier? Well, my friends at FreshBooks have the solution. FreshBooks invoicing and accounting software is designed specifically for small business owners. It’s simple, intuitive, and keeps you way more organized than a dusty shoebox filled with crumpled receipts.

It was one of the first thing I did when I started my business. I've been a FreshBooks user since 2009. It's easily the best accounting and invoicing software for small business owners like us.

Create and send professional looking invoices in 30 seconds, and then get them paid 2 times faster with automated online payments. Nothing is better than sending out an invoice and getting it paid the same day. 

File expenses even quicker, and keep them perfectly organized for tax time.

And the best part? FreshBooks grows alongside your business. So you’ll always have the tools you need when you need them - without ever having to learn the ins and outs of accounting.

Now there are a lot of features to talk about here, but I'm going to pick 2 of my favorites. The late payment reminders are clutch. It's one less thing I need to worry about when making sure I get paid. And the automated expenses are incredible. I connected my business credit card and my expenses are all there, ready for me, and my accountant, to review. It makes tax time easier for both of us.

Join the 24 million people who’ve used FreshBooks. Try it free for 30 days - no catch and no credit card required.

Go to and enter HOW I BUILT IT in the how did you hear about us section to get started.

Quick Wins

Pat Flynn talks about delivering quick wins to anyone who signs up for your email list. This develops trust. I feel I’m able to do that, thanks to ConvertKit.

Because I know what my subscribers are looking for, I can deliver curated content and helpful tips based on their needs and feedback. For example, those who signed up because they want to learn more about podcasting don’t get WordPress or web development news. They only get podcasting news and tips.

This helps me develop trust – I’m reminding my subscribers why they signed up for my email, and I’m not just selling to them. I’m hopefully helping them grow. When they’re ready to reinvest in themselves because of that growth, hopefully they’ll think of me.

But I’m not just using it for subscribers – I’m using ConvertKit for customers too. Because I know what products they’ve purchased, I can send them relevant updates about the courses (and yes, this might include other relevant courses). For my membership, I deliver a monthly behind the scenes newsletter, and notifications about office hours and exclusive live streams.

Overall it has improved my communication with everyone who’s expressed interest in my content or products.

Wrapping Up

So to quickly wrap up here, I’m using ConvertKit to understand my audience better. Using the information I’m able to gather through sign ups, link clicks, and purchases, I can send only the most relevant content to segments of my list. This makes I’m not bombarding everyone’s inbox with everything I have to say.

I’m able to do that though forms and landing pages in ConvertKit, as well as tagging, Sequences, and Automations. If you’re interested in learning more about any of that, I’ll have links in the show notes over at

And if you want to get an exclusive deal from ConvertKit, you can head over to This will let you sign up for their free plan, which allows you to make forms and landing pages. The exclusive part of the deal is that you’ll also get access to broadcasts for up to your first 100 subscribers. It’s an affiliate link, so I may get a small commission if you sign up using it, but hopefully I’ve demonstrated how valuable it is to me. Again that link is

If you liked this episode, please give it a rating and review in Apple Podcasts – it helps more people discover the show. Thanks again to our sponsors, Yith, TextExpander, and FreshBooks. These are some of my favorite tools, and I’m excited to have them on board.

How are you managing your mailing list? Do you have any questions about ConvertKit? Let me know via Twitter, @jcasabona.

Thanks so much for listening, and until next time, get out there and build something!

Free Email Course!

5 Fast Fixes to Grow Your Podcast.
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