This week on the Over Ask Podcast, Derrick Gregory joins Matt Lionetti and The Broke Agent to discuss the creative process behind his funny Instagram videos. He shares how he started making those videos and how he stays consistent with trendjacking and posting. 

He doesn’t shy away, either, from talking about the content that didn’t hit, as well as the frustration of content flops. It’s all part of learning how to overcome content struggles by experimenting and finding what kind of content you enjoy doing and that your audience loves. 

Also discussed is the importance of taking a break from producing content and why finding out what works for you is better than just copying other content creators. 

Nothing wrong with trying out someone else’s content strategy. But ultimately, if you enjoy what you’re doing, you’re far more likely to be consistent with it. 

Click on any of the timestamps below to watch: 

00:00–00:30 Intro

03:45 Derrick’s massive following on Instagram and how it all began

10:26 Consistent laughs in a market saturated with aspiring comedians

11:45 The first video that really hit—and then the first one that didn’t hit at all

17:20 Bigger productions don’t necessarily net bigger results

19:12 The joke has to be right up front (i.e., not subtle)

29:48 When you post a video and it doesn’t hit, what do the next couple days look like?

31:16 What happens to engagement when the Instagram algorithm is off (it happens)

34:24 Instagram strikes and how they affect your engagement

35:35 “A couple months ago, you took a long hiatus.” 

42:42 When you enjoy it, you’re more likely to be consistent with it. 

45:22 What are you trying to get from this other than real estate business?

Click here to watch the full episode.

This week’s Over Ask Podcast is brought to you by BoomTown. Click here to learn more.