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PODCAST

Side Hustle School

Chris Guillebeau / Onward Project

A daily show for everyone who works a regular job and wants to start an income-earning project on the side. In each episode, listeners will hear a different story of someone who"s started a side hustle—along with what went well, how that person overcame challenges, and what happened as a result. The show is written and hosted by Chris Guillebeau, the New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, and other books. Sales and Distribution by Lemonada Media

business entrepreneurship

All Episodes

6:37

Ep. 3019 - First $1,000: Miami Divorce Planner Offers...

Side Hustle School ·

2025/04/07

In this week’s First $1,000 segment, discover how a former wedding planner in Miami pivoted to organizing “freedom celebrations” for newly divorced clients, landing her first thousand dollars from two high-end events. 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:

en

6:31

Ep. 3018 - Weekend Workshop: Design Your First Workflow

Side Hustle School ·

2025/04/06

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: creating clear, repeatable systems for running your business efficiently. 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

en

4:34

Ep. 3017 - Q&A: “How do I balance transparency with...

Side Hustle School ·

2025/04/05

In this episode, we tackle the tricky balance of being transparent with your audience while maintaining professionalism. How can you build trust without oversharing or compromising your credibility? 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

en

4:23

Ep. 3016 - Q&A: “Is there still room to start a...

Side Hustle School ·

2025/04/04

Is it too late to start a podcast in 2025? In this episode, we tackle how to stand out in a crowded field and grow an audience for a niche topic. 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

en

6:03

Ep. 3015 - TBT: Bringing Tokyo’s Best Stationery to...

Side Hustle School ·

2025/04/03

In this week’s Throwback Thursday segment, learn how a stationery-lover in Tokyo began shipping curated paper goods and writing supplies abroad—all while championing small artisan shops. 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

en

8:29

Ep. 3014 - STORY: Accountant Earns $233,751 Reselling...

Side Hustle School ·

2025/04/02

A young accountant learns the art of reselling, purchasing textbooks, dental floss, and Cheerios from retail stores in bulk—then earns hundreds of thousands of dollars in profit by selling it online. 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:

en

5:25

Ep. 3013 - Q&A: “How do I find my first clients...

Side Hustle School ·

2025/04/01

In this episode, we help a new business owner attract their first paying clients without spending a dime on ads. Learn grassroots strategies for networking, social media, and building momentum from scratch. 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:

en

4:32

Ep. 3012 - First $1,000: Stay-at-Home Dad’s Virtual...

Side Hustle School ·

2025/03/31

In this week’s First $1,000 segment, find out how a stay-at-home dad turned his neighbors’ forgotten items into steady online income, taking a cut of each sale. 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:

en

8:42

Ep. 3011 - Weekend Workshop: Make It Easy to Get Paid

Side Hustle School ·

2025/03/30

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: make it easy to get paid. 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:

en

5:46

Ep. 3010 - Q&A: “How to set better boundaries with...

Side Hustle School ·

2025/03/29

In this episode, we explore how to manage client expectations when emotions get in the way. Learn how to set clear boundaries, navigate tough conversations, and keep your business running smoothly—even when clients slow down the process. 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:

en

5:32

Ep. 3009 - Q&A: “How can I work fewer hours without...

Side Hustle School ·

2025/03/28

In this episode, we help a web developer reduce his work hours while keeping his income steady. Learn how to raise rates, outsource tasks, and restructure service packages to build a smarter, more sustainable business. 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:

en

6:00

Ep. 3008 - TBT: Pet Furniture Maker Adds Digital...

Side Hustle School ·

2025/03/27

In this week’s Throwback Thursday segment, see how shifting from physical products to digital plans and online classes helped a woodworker reach more customers and streamline his business model. 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

en

7:14

Ep. 3007 - STORY: Florida Woman Gets Paid to Remove...

Side Hustle School ·

2025/03/26

In this ribetting feature, a high school science teacher earns an extra $3,000/month removing an invasive species of toads throughout Florida. 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

en

4:23

Ep. 3006 - Q&A: “How do I set the right hourly rate...

Side Hustle School ·

2025/03/25

In today’s episode, we help a social media manager set a fair hourly rate. Learn how to balance your skills and market demands to price your services confidently. 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:

en

5:58

Ep. 3005 - First $1,000: This “Crypto Tax Whisperer”...

Side Hustle School ·

2025/03/24

In this week’s First $1,000 segment, discover how an unassuming accountant turned a chaotic batch of crypto trades into a full-scale practice, complete with custom software and national training programs. 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:

en

4:46

Ep. 3003 - Q&A: “How can I get clients to provide...

Side Hustle School ·

2025/03/22

In this episode, we explore how service-based businesses can guide clients through providing accurate information. Learn how to reduce costly mistakes and protect your business! 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:

en

5:29

Ep. 3002 - Q&A: “How can I stand out in a world of...

Side Hustle School ·

2025/03/21

In today’s episode, we tackle a growing concern for creators: how to stand out in a world increasingly dominated by AI-generated content. If you’re worried about keeping your work authentic and engaging, you’re not alone. 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:

en

6:16

Ep. 3001 - TBT: Food Blog Grows to Thriving Culinary...

Side Hustle School ·

2025/03/20

In this week’s Throwback Thursday segment, learn how a recipe blogger moved beyond one-off cookbook sales to form a culinary community, offering seasonal meal plans, live demos, and valuable kitchen tool discounts. 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:

en

7:33

Ep. 3000 - STORY: “Pocket Monkey” Tool Sells 500,000...

Side Hustle School ·

2025/03/19

After getting locked out of his apartment, a software engineer creates a pocket tool that goes on to sell 500,000 units and employ 17 people. 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

en

5:27

Ep. 2999 - Q&A: “How to prioritize tasks and to-do...

Side Hustle School ·

2025/03/18

In today’s episode, we explore neurodivergent-friendly strategies to tackle an overwhelming to-do list. Learn how to work with your energy, build momentum, and stay productive without burnout. 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

en

1,405 results

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