Derrick Gregory joins Matt Lionetti and The Broke Agent to discuss the creative process for coming up with his funny videos, the frustration of content flops, why you should take a break from producing content, and how he stays consistent trendjacking and posting. 55,000+ agents choose BoomTown over any other competitor to make success easy. The best CRM in the game. Learn more about BoomTown and get equipped with all the tools you need. Try BoomTown now: https://bit.ly/BoomTownROI Matt Lionetti: https://www.instagram.com/matt.lionetti/ The Broke Agent: https://www.instagram.com/thebrokeagent/ Derrick Gregory: https://www.instagram.com/derrickswflrealtor/ Listen and Subscribe: Apple Podcasts: https://podcasts.apple.com/us/podcast/over-ask/id1547905792 Timestamps: 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?