Ep. 3374 - Q&A: “Should I offer a pay-what-you-will price?”
Side Hustle School
Chris Guillebeau
4.7 • 3.3K Ratings
🗓️ 28 March 2026
⏱️ 7 minutes
🧾️ Download transcript
Summary
This listener started a pen-to-paper initiative to connect people through snail mail. It's starting well, but how can it scale—and is a Pay-What-You-Will pricing model the best option?
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.
Show notes: SideHustleSchool.com
Email: team@sidehustleschool.com
Be on the show: SideHustleSchool.com/questions
Connect on Instagram: @193countries
Visit Chris's main site: ChrisGuillebeau.com
Read A Year of Mental Health: yearofmentalhealth.com
If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼
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.
Show notes: SideHustleSchool.com
Email: team@sidehustleschool.com
Be on the show: SideHustleSchool.com/questions
Connect on Instagram: @193countries
Visit Chris's main site: ChrisGuillebeau.com
Read A Year of Mental Health: yearofmentalhealth.com
If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼
Hosted on Acast. See acast.com/privacy for more information.
Transcript
Click on a timestamp to play from that location
| 0:00.0 | Should you offer a pay what you will price? |
| 0:08.7 | Should you be like, hey, potential customers, I have this item or service or whatever it is. |
| 0:14.2 | I've got something for sale. |
| 0:15.5 | I would love for you to buy it. |
| 0:16.9 | And you can tell me what the price is. |
| 0:19.6 | Like you decide. |
| 0:20.5 | I don't want to make that decision so you can decide. Or maybe you pay what you're able, whatever you think it's worth. You know, there could be a few different ways to do it. Should you do that? Like as a business owner or a side hustler, when you're thinking through your process of setting up payments, should this be an option? And we're going to hear today from a listener. They started a |
| 0:37.8 | pen to paper initiative to connect people through snail mail. So that's pretty cool. Interesting |
| 0:43.8 | business model. Seems like it's starting well. And they're wondering, let's see, what is it? |
| 0:48.6 | They're wondering, well, they're wondering, you know, how will it scale, can it scale? And what I think about the Choose What You Pay price model. |
| 0:57.0 | Okay. Well, I'm going to give you a direct opinion as I like to do. It's not helpful to give you a |
| 1:02.4 | wishy-washy opinion, right? So it's fine if you disagree, but I will be direct. I'm going to |
| 1:07.1 | give that detailed answer, followed by the detailed question from our listener. |
| 1:11.6 | Stay tuned. It's coming right up. |
| 1:14.4 | I make thanks to our partner, Notion, for sponsoring today's episode. |
| 1:18.2 | Notion is a pretty cool tool. I've been using it for years. And now they've got something new. |
| 1:23.1 | Notions, all new custom agents. Custom agents. Just imagine if like all of the quick questions that you get from email or direct messages or something else, what if they disappeared? |
| 1:34.2 | And an AI agent took care of them, but also did a good job, you know? |
| 1:38.3 | Well, with Notion's new custom agents, the busy work is handled. |
| 1:41.5 | A Q&A agent can pull from your existing knowledge and |
| 1:44.2 | Notion share answers directly in Slack so your team gets the instant answers it needs without |
| 1:49.3 | constantly interrupting your own work. I've been playing around with custom agents. It is a fun |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from Chris Guillebeau, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of Chris Guillebeau and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2026.

