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

03/07/25 • 73 min

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...

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/

•••
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:

Previous Episode

He Left Amazon, Then Made $1M Online (w/ Daniel Vassallo) | 042

Dillan interviews Daniel Vassallo—an ex-Amazon engineer who quit the 9-5 grind to pursue building his own projects online.
Daniel runs the Small Bets community, with thousands of creators and entrepreneurs who want to make low-risk, low-pressure experiments when it comes to building online businesses.
They discuss: why Daniel hates Y-Combinator, what a "small bet" actually is, Daniel's biggest business mistakes, why Daniel quit his cushy job at Amazon, why most entrepreneurs fail, what woodworking taught Daniel about building businesses, how to structure your workflows, how Daniel accidentally started a profitable online community, tips for building a strong online community, how Daniel sold access to his calendar, and much more.
Daniel's links...
Twitter / X: https://x.com/dvassallo
Small Bets: https://smallbets.com/
•••
Follow Dillan on the interwebs...

•••
0:00 Intro
1:07 Daniel hates YC
7:03 Why he quit Amazon
21:18 Worst-case scenario
28:28 Dose & frequency
40:31 High vs low motivation tasks
48:22 Burning the boats
52:58 Your "why" doesn't matter
58:04 How Small Bets started
1:15:06 Online community tips
1:31:32 Daniel's latest small bet

Next Episode

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

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...

•••
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