The Harsh Reality of Being a Full-Time Creator (w/ CupppaJoe5) | 044

04/07/25 • 77 min

Dillan interviews Joe (@CupppaJoe5). He's a Call of Duty: Warzone creator and educator, helping his audience improve at the game. A year ago, he quit his 9-5 job to do content full-time.
They discuss: the best and worst parts of being a full-time content creator, why Joe started a brand new channel from scratch, why being stuck in a niche isn't a bad thing, what Joe learned from starting a new YouTube channel, how to script your videos in a way that attracts new viewers, the most valuable mistakes Joe has made, all of Joe's different revenue streams as a creator, why you should raise your prices, what Joe wishes he knew when he quit his job to do content full-time, and much more.
Joe's links...
Website: https://cupppajoe5.com/
Twitter / X: https://x.com/CupppaJoe5
YouTube main: https://www.youtube.com/c/CupppaJoe5
YouTube let's play: https://www.youtube.com/@CupppaJoePlays
•••
Follow Dillan on the interwebs...

Twitter / X: https://x.com/dillanroytaylor
Newsletter: https://www.grindstone.coach/newsletter
Apply for Grindstone Coaching: https://www.grindstone.coach/Music by myboy.scoochy:
https://www.instagram.com/myboy.scoochy/

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0:00 Intro
0:49 Easiest / hardest part?
7:53 Why Joe started a new channel
12:51 Being "trapped" in a nice
23:12 Lessons from the new channel
29:13 How to talk to new viewers
35:19 Joe's most valuable mistakes
39:23 Rev stream 1: YouTube adsense
42:45 Rev stream 2: streaming
49:32 Rev stream 3: coaching
54:36 Why you should raise your prices
1:01:36 Rev stream 4: TikTok
1:05:56 Rev stream 5: sponsorships
1:10:14 Joe's advice to his past self
1:15:28 Bye bye bye

Previous Episode

How a Newsletter Revived This Chess Master's Career (w/ Nate Solon) | 043

Dillan interviews Nate Solon—a chess coach, writer, and FM (FIDE Master) in chess. There are only about 9000 FMs in the world, which means Nate is in the top .3% of all chess players on the planet.
Nate writes the Zwischenzug newsletter, built a nice Twitter audience, made a few chess courses on Chessable, and even wrote a chess book. Nate uses his data science background in his content to help intermediate chess players study and improve at the game.
They discuss: how Nate revived his chess career after a long hiatus, how Nate grew an audience through long-form writing in a world of video content, Nate’s sales funnel for getting chess coaching students, how Nate builds Chessable courses, why Nate started and closed down a paid community, and at the end of the convo Nate and Dillan play a quick blitz game.
Nate's links...
Website / Coaching / Courses: https://www.natesolon.com/
Twitter / X: https://x.com/natesolon
Newsletter: https://zwischenzug.substack.com/
•••
Follow Dillan on the interwebs...

•••
0:00 Intro
1:37 Nate's chess career
5:05 What's an FM?
10:10 Why Nate started content
15:07 Can anyone make a chess course?
20:43 How Nate advertised
25:41 Types of chess content
28:11 Niche vs broad
35:54 Nate's ideal audience
39:27 Nate's paid community
44:

Next Episode

Why She Quit Her Successful Podcast (w/ Michelle Varghese) | 045

Dillan interviews Michelle Varghese—a writer and former podcaster who co-hosted Build a Wealthy Spirit for four years with her sister.
Now focused on writing and coaching, Michelle helps nonfiction creators improve their craft and grow their audience.
They discuss: why Michelle and her sister intentionally quit their podcast after four consistent years, how to know when you're truly done with a creative project, the identity crisis that can follow quitting, how creators can build systems to stay consistent, what Michelle learned from podcasting that she now applies to her writing business, the importance of marketing your work (even when it feels uncomfortable), what the word "niche" actually means, how to gracefully pivot your creator brand, the rise of personality-driven content in the age of A.I., why vulnerability and in-person connection are the future of content, and much more.
Michelle's links...
Website: https://michelleelisabethvarghese.com/
Twitter / X: https://x.com/mvarghoose
Writing coaching: https://michellevarghoose.gumroad.com/l/writingcoaching/
•••
Follow Dillan on the interwebs...

•••
0:00 Intro
0:58 Why Michelle and her sister quit their podcast
3:22 How to know when to quit a project
6:47 The identity shift that comes from quitting
10:53 Top 3 lessons from running a weekly podcast
15:53 The Ford ad story: why repetition matters
20:53 How creators can build systems to stay consistent
26:33 Moving on from being “the sabbatical girl”
30:51 The risks of changing your niche
35:23 Being your own niche in the age of A.I.
36:53 Vulnerability and in-person connection
42:46 Michelle’s “topics vibe, & connection”
50:33 Launching her writing coaching
55:30 Bye bye bye