Ep. 3413 - Q&A: “How can I sell my own crossword puzzles?”
Side Hustle School
Chris Guillebeau
4.7 • 3.3K Ratings
🗓️ 7 May 2026
⏱️ 5 minutes
🧾️ Download transcript
Summary
A listener is all crossed up in her quest to make and sell crossword puzzles.
Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.
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Transcript
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| 0:00.0 | How can you make and sell your own crossword puzzles? |
| 0:11.5 | That's what we've got today from a caller. |
| 0:14.4 | Caller in, well, I was going to say, where are they? |
| 0:16.8 | I'm not sure what their location is. |
| 0:18.1 | Maybe that's not even pertinent. |
| 0:20.0 | What is pertinent is her quest to make and sell crossword puzzles. Now, as you may be aware, millions of people complete crosswords every day. It is, in fact, the original Pokemon. Well, I'm not totally sure that analogy makes sense. But the point is, lots and lots of people do crossword puzzles. They've been doing it for a long time. You've got the New York Times crossword now. The New Yorker has one. USA Today has a crossword. There are many, many other |
| 0:42.0 | independent ones as well. So what are the business opportunities for someone who is one of these |
| 0:46.9 | hobbyists and doesn't want to just complete the crossword, but actually go about making and selling |
| 0:53.9 | them? And what are the obstacles that she |
| 0:55.7 | might need to overcome? So that's what we're going to hear about today from Jessica. Well, she's |
| 1:00.2 | going to ask this question. And I did a little bit of research to make sure I can give her a helpful |
| 1:04.5 | answer. Maybe it'll get somebody else out there thinking about their idea as well. Detailed question |
| 1:09.1 | from Jessica. Coming right up. |
| 1:23.4 | Hi, Chris. This is Jessica, and I love crossword puzzles. After many years of completing them every day, |
| 1:30.6 | I'm ready to design my own. There are lots of resources that explain how to do this, and I think I've |
| 1:37.0 | got that part figured out. Or at least I'm on track. What I don't know, though, is how to sell them. The New York Times and USA Today |
| 1:46.6 | crosswords are completed by millions of people every day, and my sense is that they have a near |
| 1:52.2 | monopoly on the market. I can't compete with them. Is there another path to getting my crosswords |
| 1:58.9 | out to a dedicated fan base? Thanks, Chris, and looking |
| 2:02.8 | forward to hearing from you. Well, Jessica, I think even though the New York Times and USA |
| 2:11.1 | today, Crosswords are pretty big and they're completed by millions of people, I don't think |
| 2:15.3 | you're really competing with them. I don't actually think they have a near monopoly on the market. And in fact, sometimes people discover crosswords through |
... |
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