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Side Hustle School

Ep. 3390 - First $1,000: “I cold-pitched 10 brands and got my first 2 clients…”

Side Hustle School

Chris Guillebeau

Business, Side Hustle, Small Business, Careers, Entrepreneurship,, Entrepreneurship

4.73.3K Ratings

🗓️ 13 April 2026

⏱️ 7 minutes

🧾️ Download transcript

Summary

In this week's First $1,000 segment, we hear from a freelance apparel designer who specializes in menswear. After having her first child, she set out to learn to work on her own. 

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

When you run a business, every minute counts. An accounts payable can take up way more time than it should.

0:06.9

That's why I recommend Intuit QuickBooks Bill Pay. QuickBooks Bill Pay automates your accounts payable in QuickBooks.

0:13.3

So you're not sending invoices at midnight or chasing vendors on your lunch break.

0:17.1

With QuickBooks Bill Pay, all your bills, vendor records, 1099s, financial reports, all that stuff.

0:22.4

It all lives in one simple dashboard.

0:24.4

No more manual bill entry.

0:26.2

You instantly see what's due, and you choose how and when money goes out.

0:30.2

You stay in control.

0:31.8

Spend less time on admin and more time keeping your business growing with QuickBooks Bill Pay.

0:36.3

Learn more at QuickBooks.com

0:37.7

slash bill pay. Again, that's quickbooks.com slash bill pay. Terms apply. Money movement

0:43.3

services are provided by Intuit Payments Incorporated. License as a money transmitter by the New

0:47.5

York State Department of Financial Services.

1:00.1

I cold pitched 10 brands and got my first two clients.

1:01.5

Welcome, friends.

1:04.4

Welcome to SaitoSool School, your host, Chris Gillibow here.

1:09.5

In this week's first $1,000 segment, we're going to hear from a freelance apparel designer who specializes in menswear.

1:11.4

After having her first child, she sets out to learn to work on her own. And as I mentioned in that

1:17.6

little headline, she cold pitches 10 brands and gets her first two clients. So if you are

1:23.0

thinking about starting a little business or offering a service and you're like, well, I don't

1:27.1

want to go out and email a bunch of people or message them on LinkedIn. Well, no doubt there is a bad way to do

1:33.1

that, a way that is just going to be a waste of your time and everybody else's time as well.

...

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