Ep. 3244 - Q&A: “How do I upsell without sounding pushy?”
Side Hustle School
Chris Guillebeau
4.7 • 3.3K Ratings
🗓️ 18 November 2025
⏱️ 7 minutes
🧾️ Download transcript
Summary
Great contracting work often reveals the next problem to solve. Here's a simple script that turns an “upsell” into an obvious win for the client—and leaves everyone feeling good about the extra invoice.
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
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| 0:00.0 | If you ever shop online, which, let's be real, who doesn't, you already understand how important |
| 0:05.6 | customer reviews are. You know this as a consumer, right? You always check the reviews before you buy |
| 0:10.1 | something and your customers are checking reviews as well. That's why if you run an e-commerce |
| 0:14.7 | business, reviews have an enormous impact on your business and you want to level up your business |
| 0:19.0 | to get better reviews. You can do that with |
| 0:21.1 | our longtime partner ShipStation. It is a fantastic service that has served so many of our listeners |
| 0:26.7 | as well. I highly recommend it while your customers and get rave reviews with cheaper, |
| 0:31.2 | faster, and better shipping. Upgrade to ShipStation today to get a 60 day free trial at shipstation.com |
| 0:37.2 | and use code hustle. No credit card or |
| 0:39.7 | contract required and you can cancel any time. That's shipstation.com code hustle. |
| 0:48.2 | Lemonada. |
| 0:52.9 | Let's talk about upselling. How can you successfully upsell without sounding pushy? |
| 1:02.6 | And the thing about upselling is we all encounter upselling all the time. And there's a way that it happens that actually feels totally normal and natural and not |
| 1:11.7 | annoying at all. And we've all been on the other side of things where it's like somebody keeps |
| 1:16.3 | pushing. Would you like this? Would you like that? And you're like, this is just too much, dude. |
| 1:20.6 | So it can go either way. But I encourage you to think about how could you take the products or services |
| 1:25.3 | you're offering whatever offer you're trying to |
| 1:27.6 | develop and think about, you know, what are the logical extensions or upgrades that this person |
| 1:33.1 | might want to create that environment where people are happy to say yes. So we're going to try to |
| 1:38.7 | give a script, going to give a script to our caller today that turns an upsell into an obvious |
| 1:42.7 | win for the client, leaving |
| 1:44.5 | everybody feeling good about that extra invoice. Done with care, offering additional help is not |
... |
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