How Did You End Up Doing That?

Matt Ragland is a productivity expert and full-time content creator. He has worked for companies such as AppSumo.com, ConvertKit, and Podia. Matt graduated from the University of Florida with a bachelor’s degree in recreation & tourism management.

Matt was one of the earliest members of the team at ConvertKit, where he was employee number five. Since leaving ConvertKit to start his own company, he now hosts a podcast, publishes a newsletter, has created several courses, and hosts his own YouTube channel.

Matt prides himself on being a skilled manager and enjoys helping his clients and audience grow and develop their agencies. He is also the proud father of two boys and is a fitness enthusiast. Matt and his family live in Nashville, Tennessee.

In this episode, you’ll learn:

• Matt’s biggest revenue drivers as a content creator
• How to know when it’s time to take your side hustle full-time
• How to optimize your YouTube channel and content

Links & Resources

• Podia
• Ryan Delk
• Bryan Harris
• James Clear
• Sean McCabe
• Sean McCabe
• Levi Allen
• Casey Neistat
• Tim Ferriss
• Jeff Goins
• Ali Abdaal
• Marques Brownlee
• Roberto Blake
• heycreator.com

Matt Ragland’s Links

• Follow Matt on Twitter
• Watch Matt on YouTube
• Matt’s website
• Matt's newsletter

Episode Transcript

Matt: [00:00:00]
If you’re not sure if you want to do something, try it 10 times, and really give it a good try. Write 10 newsletters. Make 10 videos on YouTube. Record 10 podcasts. I have found that going from 10 to a hundred is definitely a slog, and there are lots of mini milestones, but once you do something a hundred times, you’re going to build momentum on it.

And you’re also going to build your own country.

Nathan: [00:00:30]
In this episode I talk to my long-time friend, Matt Ragland. So Matt joined ConvertKit really in the early days. He was employee number five, and he was here for the crazy ride. Then he started a YouTube channel. He led the customer experience team at another startup called Podia. He’s now as a full-time independent creator earning a living on his own.

We have a really fun conversation reminiscing about the early days talking about crazy rocket ship growth, and how we kept up. We get into earning a living as a creator. How he grew his YouTube channel to 60,000 subscribers. How to choose a niche, and when you should double down on that, and what’s getting traction on YouTube.

The last thing that we talk about is when, as a creator, you should quit your full-time job, and some of the nuances of that, so you can go full-time on your creative endeavor. So it’s a longer episode today because Matt and I just can’t help but tell stories.

With that, let me get out of the way and dive in.

Matt, thanks for joining me.

Matt: [00:01:31]
Oh, it’s such a pleasure. I’m thrilled to be here.

Nathan: [00:01:34]
I want to go back to, what year would it even be?

Matt: [00:01:40]
2015.

Nathan: [00:01:41]
2015? Okay.

Matt: [00:01:44]
Right around this time. Maybe a couple months later, but it was like late summer.

Nathan: [00:01:49]
So, it’s July, like yeah. And then July right now. Yeah, it would have been when we started talking, I’m thinking, what were you doing online around that time? Cause I started to come across you on Twitter.

I think Brian Delk was a mutual friend.

Is that right?

Matt: [00:02:06]
Yeah. Ryan Delk was a mutual friend. Brian Harris was a mutual friend. The way that we got actually directly connected is that I was on Brian’s email list. And I saw that you were doing a webinar with him to promote ConvertKit. And I had just signed up for ConvertKit as a customer, always like a little notch in the cap that I, I feel like I have of having like the three-digit user ID.

Nathan: [00:02:32]
Do you remember what your user ID is?

Matt: [00:02:33]
I used to know.

Nathan: [00:02:36]
In the three digits is pretty impressive.

Matt: [00:02:38]
Yeah. A three digit. Yeah, definitely.

Nathan: [00:02:41]
Now they’re well into the six digits.

Matt: [00:02:43]
Yeah, it’s wild. And so, I was familiar with ConvertKit. Certainly at that time it was like, okay, let me watch Nathan talk about it. What are the things that he thinks are important with it? Like some email building strategies? Because what I was really doing a lot of my online work at that time is I was doing two things.

I was doing some contract work with some other SaaS companies. In terms of an audience building creator standpoint, I was doing two things. One was that I was creating the sketch notes. And so like visual, visual art of like webinars, podcasts. And that’s what I would use to teach people how to take better notes so they could remember more of what they’re doing.

And it was a way to connect with other influencers because it was an attention grabbing thing. And so that was the main thing in terms of audience building and some course creation.

The other thing that I was doing that paid the bills a little bit better at that time was I was also helping people set up WordPress themes and websites.

At the time I would be like, oh yeah, you know, I kind of do some web development and then like, not really knowing like what all that meant. And then as I started to work more and more with actual developers, I would set up a theme online for people. But you also look at it and see that there’s still a pretty interesting intersection between like, how can you just do something relatively simple for people that either: A, they don’t have time to do, or B, they just don’t want to figure out because they just want to focus on their creative work.

And so that’s what I was doing summer 2015 at the time.

Nathan: [00:04:27]
Yeah. So then at the time we were, I think four people, five people on the, let me count,

Matt: [00:04:37]
I think it was four if I remember properly,

Nathan: [00:04:39]
Myself, mark, David, Dan.

Four. Yeah. and we were at 15,000 a month in revenue. Let’s see now I’m trying to think.

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