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Side Hustle School podcast

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Side Hustle School

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  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 [https://lemonadamedia.com/] (https://lemonadamedia.com/)

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 [https://lemonadamedia.com/] (https://lemonadamedia.com/)

 

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Duration

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#3325

Ep. 3270 - Weekend Workshop: From Rock Bottom to Business Empire

This new segment is all about helping you learn the key steps to a new side hustle in 2025... more

Yesterday

07 MINS

07:01

Yesterday

#3324

Ep. 3269 - Q&A: “What do I do if my partner doesn’t believe in my business?”

In this episode, a listener wants support at home without abandoning a dream. We’ll ... more

13 Dec 2025

04 MINS

04:53

13 Dec 2025

#3323

Ep. 3268 - Q&A: “Are Instagram links killing my reach?”

A listener worries external links are throttling her posts. We’ll use Instagram-nati... more

12 Dec 2025

05 MINS

05:44

12 Dec 2025

#3322

Ep. 3267 - TBT: Hand-Written Recipes Become Kitchen Wall Art

In this week’s Throwback Thursday segment, discover how one maker rescued stained re... more

11 Dec 2025

05 MINS

05:56

11 Dec 2025

#3321

Ep. 3266 - STORY: Marathon Runner Earns Full-Time Income Trying On Shoes

A decade-long “marathon distance” project earns six-figures in affiliate commi... more

10 Dec 2025

07 MINS

07:29

10 Dec 2025

#3320

Ep. 3265 - Q&A: “Should I add shipping to my Marketplace listings?”

A local-only seller is debating shipping. We’ll cover when it’s worth it, the ... more

09 Dec 2025

05 MINS

05:37

09 Dec 2025

#3319

Ep. 3264 - First $1,000: Flipping Rolling Carts & Filing Cabinets

In this week’s First $1,000 segment, dull beige cabinets became hot pastel storage a... more

08 Dec 2025

06 MINS

06:43

08 Dec 2025

#3318

Ep. 3263 - Weekend Workshop: The Never Boss Philosophy

This new segment is all about helping you learn the key steps to a new side hustle in 2025... more

07 Dec 2025

08 MINS

08:14

07 Dec 2025

#3317

Ep. 3262 - Q&A: “Should I raise my coaching rates or add more clients?”

Today’s caller has two levers—charge a bit more or work a bit more. We’l... more

06 Dec 2025

05 MINS

05:15

06 Dec 2025

#3316

Ep. 3261 - Q&A: “Is my struggling side hustle worth saving?”

A listener wants to know if a slow start is normal, or a warning sign that another busines... more

05 Dec 2025

05 MINS

05:49

05 Dec 2025

#3315

Ep. 3260 - TBT: Campaign Scheduling Tool Turns Out Voters

In this week’s Throwback Thursday segment, find out how a small campaign tool turned... more

04 Dec 2025

05 MINS

05:21

04 Dec 2025

#3314

Ep. 3259 - STORY: Accountant Earns Six-Figures Selling Spreadsheets to Etsy Sellers

She was burned out being a CPA, so she turned her efforts to an Etsy business—but it... more

03 Dec 2025

07 MINS

07:38

03 Dec 2025

#3313

Ep. 3258 - Q&A: “Can I profit from flipping open-box customer returns?”

Today’s listener wants to turn store returns into cash. We’ll cover how to eva... more

02 Dec 2025

04 MINS

04:59

02 Dec 2025

#3312

Ep. 3257 - First $1,000: DIY Headshot Stations for University Job Fairs

In this week’s First $1,000 segment, campus recruiters needed polished LinkedIn phot... more

01 Dec 2025

05 MINS

05:35

01 Dec 2025

#3311

Ep. 3256 - Weekend Workshop: Building Teams Without Hiring Employees

This new segment is all about helping you learn the key steps to a new side hustle in 2025... more

30 Nov 2025

07 MINS

07:51

30 Nov 2025

#3310

Ep. 3255 - Q&A: “When is uneven side-hustle income safe to rely on?”

Today’s caller makes more money on weekends than at the day job—but their reve... more

29 Nov 2025

04 MINS

04:44

29 Nov 2025

#3309

Ep. 3254 - Q&A: “How do I price my VA work for true value?”

If clients praise your speed but you’re still billing like a beginner, it’s ti... more

28 Nov 2025

04 MINS

04:31

28 Nov 2025

#3308

Ep. 3253 - TBT: Scarce Lego Sets Build Value Over Time

In this week’s Throwback Thursday segment, find out how one patient side hustler sto... more

27 Nov 2025

06 MINS

06:18

27 Nov 2025

#3307

Ep. 3252 - STORY: Frenchman Says Bonjour to $35,000/Month Foodie Hustle

After relocating to Quebec, this continental creative brings seasonal flavor to an artisan... more

26 Nov 2025

08 MINS

08:02

26 Nov 2025

#3306

Ep. 3251 - Q&A: “Is my burnout a signal to pivot?”

Are you just tired—or do you need a bigger break? In this episode, we’ll help ... more

25 Nov 2025

05 MINS

05:13

25 Nov 2025

#3305

Ep. 3250 - First $1,000: Digital Window Menu Boards for Food Trucks

In this week’s First $1,000 segment, a designer helps food trucks and pop-up restaur... more

24 Nov 2025

06 MINS

06:00

24 Nov 2025

#3304

Ep. 3249 - Weekend Workshop: From Ski Bum to Six-Figure Teacher

This new segment is all about helping you learn the key steps to a new side hustle in 2025... more

23 Nov 2025

07 MINS

07:07

23 Nov 2025

#3303

Ep. 3248 - Q&A: “Should I spend $2,000 on retention or acquisition?”

Today’s caller runs a tiny subscription app and has two grand to spend. Should that ... more

22 Nov 2025

05 MINS

05:18

22 Nov 2025

#3302

Ep. 3247 - Q&A: “Instagram, TikTok, or LinkedIn—how do I choose?”

Posting everywhere spreads you thin; posting in the right place compounds momentum. Today ... more

21 Nov 2025

05 MINS

05:25

21 Nov 2025

#3301

Ep. 3246 - TBT: Recruiters Pay Me to Tear Apart Their Emails

In this week’s Throwback Thursday segment, hear how one copy-savvy side hustler turn... more

20 Nov 2025

05 MINS

05:38

20 Nov 2025