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Side Hustle School

Ep. 3244 - Q&A: “How do I upsell without sounding pushy?”

Side Hustle School

Chris Guillebeau / Onward Project

Business, Entrepreneurship, Careers

4.83.3K 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

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Transcript

Click on a timestamp to play from that location

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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