Side Hustle School

Ep. 3544 - First $1,000: “I have 3 clients and $4,000/month in retainer fees…”

Mon, 14 Sep 2026 07:00:00 GMT

In this week’s First $1,000 segment, we hear from a Social Media Manager from Toronto. She has a day job she enjoys but—naturally—also has a side hustle that’s bringing in $4,000 a month.

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.

Side Hustle School

Ep. 3544 - First $1,000: “I have 3 clients and $4,000/month in retainer fees…”

Ep. 3543 - STORY: Professor Starts Marvel-ous YouTube Channel

Ep. 3542 - Q&A: “Can you still get paid to post pins on Pinterest?”

Ep. 3541 - STORY: American Woman Starts International Whisky Brand

Ep. 3540 - TBT: Blogger Explores Affiliate Marketing in India

Ep. 3539 - Q&A: “How about a directory of garage and yard sales?”

Ep. 3538 - Q&A: “I have 20 years of experience—how do I pick a niche?”

Ep. 3537 - First $1,000: “I wanted to be the guy with a laptop on the beach…”

Ep. 3536 - STORY: BBQ Catering Hustle Smokes Out Competitors

Ep. 3535 - Q&A: “I’m getting too many inquiries…”

Ep. 3534 - Failure Friday: “My anniversary sale was an epic fail…”

Ep. 3533 - TBT: “Chewable Energy” Gum Sticks With Customers

Ep. 3532 - Q&A: “I want to be a broker for overseas web developers…”

Ep. 3531 - Q&A: “Can I pursue public speaking as a side hustle?”

Ep. 3530 - First $1,000: “I help people get back their hacked accounts…”

Ep. 3529 - STORY: Anchors Aweigh! Designer Leads Guided Sailing Tours

Ep. 3528 - Q&A: “Is it still possible to start a blog?”

Ep. 3527 - STORY: Cake Artist’s Confections Whisk Up Delicious Profits

Ep. 3526 - TBT: Tap Dance Teacher Offers Worldwide Lessons

Ep. 3525 - Q&A: “Should I self-publish a mental health guidebook on Kindle?”

Ep. 3524 - Q&A: “I’d like to be a financial advisor for Gen Z…”

Ep. 3523 - First $1,000: “I wanted to explore AI-generated art…”

Ep. 3522 - STORY: Lather, Rinse, Recycle: Soapy Problem Leads to Clean Solution

Ep. 3521 - Q&A: “How do I find customers as a digital personal assistant?”

Ep. 3520 - Failure Friday: “After I was hit by a car, things got worse…”

Ep. 3519 - TBT: Bridesmaid-for-Hire Keeps Walking Down the Aisle

Ep. 3518 - Q&A: “Where do I begin if I want to make an app?”

Ep. 3517 - Q&A: “Should I start a new site for my food business?”

Ep. 3516 - First $1,000: “I built an Airbnb rental in my backyard…”

Ep. 3515 - STORY: Hair Braiding Workshops Help Trans-Racial Adoptive Families

Ep. 3514 - Q&A: “How to make a board game from start to finish?”

Ep. 3513 - STORY: Teacher Flips Sports Gear For $8,000/Month

Ep. 3512 - TBT: Southern Transplant Creates Watercolor Brand

Ep. 3511 - Q&A: “Do I have to sell as a SAAS?”

Ep. 3510 - Q&A: “How many tech tools do I need to master?”

Ep. 3509 - First $1,000: Paralegal Assists U.S. Immigrants to Canada

Ep. 3508 - STORY: “SwitchPod” Camera Tool Raises $415,748 on Kickstarter

Ep. 3507 - Q&A: “How to convert non-paying students into customers?”

Ep. 3506 - Failure Friday: “I had tears in my eyes reading the response…”

Ep. 3505 - TBT: Family Affirmation Cards Go Global

Ep. 3504 - Q&A: “How do you forecast earnings for a side hustle?”

Ep. 3503 - Q&A: “Ideas for an architect trying to change business models?”

Ep. 3502 - First $1,000: The Pacific Northwest Tiny Home Designer

Ep. 3501 - STORY: Networking Success Is Served with Side of Eggs

Ep. 3500 - Q&A: “What's the best way to sell a digital download?”

Ep. 3499 - STORY: Hedge Fund Manager Rocks On with Diamond Algorithm

Ep. 3498 - TBT: Hydroponic Indoor Plant System Branches Out

Ep. 3497 - Q&A: “How much time do people spend on these projects?”

Ep. 3496 - Q&A: “How to sell an online birth preparation course?”

Ep. 3495 - First $1,000: Vintage Luggage Upcycler Hits Ground Running

Ep. 3494 - STORY: The 50 Shades of Editing Romance Novels

Ep. 3493 - Q&A: "I sold more by raising my prices—is that wrong??”

Ep. 3492 - STORY: Failure Friday: “My business partner was a convicted felon…”

Ep. 3491 - TBT: “Kindness Kits” Spread Love and Draw Positive Returns

Ep. 3490 - Q&A: “How can I make a product to help with applied learning?”

Ep. 3489 - Q&A: “I’d like to sell an Apple Watch guide…”

Ep. 3488 - First $1,000: “I had literally zero intention of running a business…”

Ep. 3487 - STORY: Chemical Engineer Zips Up Solution for Baggy Shirts

Ep. 3486 - Q&A: “I’d like to sell a toolkit to sole proprietors…”

Ep. 3485 - STORY: Atlanta Lawyer Walks Into Food Tour Biz

Ep. 3484 - TBT: Multilingual Insurance Agent Creates Translation Course

Ep. 3483 - Q&A: Are there any *good* MLM companies?

Ep. 3482 - Q&A: “Recovering after a failed partnership…”

Ep. 3481 - First $1,000: Indian Woman Helps Indian Men Improve Dating Profiles

Ep. 3480 - STORY: Aerospace Apprentice Soars to Seven-Figure Heights

Ep. 3479 - Q&A: “Is reselling gift cards a viable idea?”

Ep. 3478 - Failure Friday: “I tried to sell something no one wanted…”

Ep. 3477 - TBT: “Hero’s Journal” Completes Epic Quest

Ep. 3476 - Q&A: “How to find markets for livestreaming events?”

Ep. 3475 - Q&A: “How to best use a time of unemployment?”

Ep. 3474 - First $1,000: “I had no idea Hula Hoops were a seasonal business…”

Ep. 3473 - STORY: Enjoy an Ice Cold Beverage in a Mug Made from Ice

Ep. 3472 - Q&A: “How should I promote my new app?”

Ep. 3471 - STORY: Tinder Matched Couple Swipes Right to Sell Cupcakes

Ep. 3470 - TBT: Comfy Pillow Provides Seatbelt Support for Cancer Patients

Ep. 3469 - Q&A: “Where's the best place to hire contractors?”

Ep. 3468 - Q&A: “How do you determine a customer’s emotional needs?”

Ep. 3467 - First $1,000: “Clients don’t want Wordpress, they want a website…”

Ep. 3466 - STORY: Music Graduate Makes Spare Change Filling Spare Rooms

Ep. 3483 - Q&A: Are there any good MLM companies?