Side Hustle School

Business

Side Hustle School

by 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/

103 episodes

EN language

All Episodes

1

Ep. 3360 - Q&A: “How to start a meal prep side hustle?”

5:36 Mar 14, 2026

2

Ep. 3359 - STORY: Working Mother Sells Coats to Buckle in Babies

7:30 Mar 13, 2026

3

Ep. 3358 - TBT: Rosary Beads Count Off Extra Income

6:56 Mar 12, 2026

4

Ep. 3357 - Q&A: “How can I get paid to help resellers?”

5:32 Mar 11, 2026

5

Ep. 3356 - Q&A: “I’m a professional speed skater. How can I fundraise?”

4:53 Mar 10, 2026

6

Ep. 3355 - First $1,000: Camping YouTuber Earns Affiliate Income

6:02 Mar 9, 2026

7

Ep. 3354 - STORY: “Productivity Nannies” Dig Co-Working Caves for Modern Workers

6:59 Mar 8, 2026

8

Ep. 3353 - Q&A: “One-page business plan: what is the essential info?”

4:57 Mar 7, 2026

9

Ep. 3352 - Failure Friday: “Our first trade show was canceled with no refund…”

8:00 Mar 6, 2026

10

Ep. 3351 - TBT: The Tennessee Bachelorette Party Boom

6:09 Mar 5, 2026

11

Ep. 3350 - Q&A: “What are the most profitable niches for teaching?”

6:38 Mar 4, 2026

12

Ep. 3349 - Q&A: "I'm opening a new hair salon. How can I build my clientele?”

5:39 Mar 3, 2026

13

Ep. 3348 - First $1,000: “I earn $3,000/month leading London walking tours…”

6:14 Mar 2, 2026

14

Ep. 3347 - STORY: Trader Joe’s Sign Artist Earns $43,200 Selling Tea-Stained Prints

6:39 Mar 1, 2026

15

Ep. 3346 - Q&A: “I'm being headhunted... for my side hustle!”

4:18 Feb 28, 2026

16

Ep. 3345 - STORY: Beard Oil Behemoth Expands to 35 Countries

6:58 Feb 27, 2026

17

Ep. 3344 - TBT: iPhone App Tracks Weight-Loss Progress

6:00 Feb 26, 2026

18

Ep. 3343 - Q&A: “How to break out of a sales slump?”

4:31 Feb 25, 2026

19

Ep. 3342 - Q&A: “What’s the best way to register domains?”

4:10 Feb 24, 2026

20

Ep. 3341 - First $1,000: “Hyperfluent” Language Service Translates Into Profit

7:28 Feb 23, 2026

21

Ep. 3340 - STORY: Proud Mainer Brings Whoopie Pies to the World

8:17 Feb 22, 2026

22

Ep. 3339 - Q&A: “What kind of review platform would be best for online learning?”

5:24 Feb 21, 2026

23

3338 - Failure Friday: “They just weren’t interested in what we were selling…”

7:26 Feb 20, 2026

24

Ep. 3337 - TBT: The Mushroom Kingdom of North Carolina

8:00 Feb 19, 2026

25

Ep. 3336 - Q&A: “Is there a way to trade plane tickets for profit?”

4:52 Feb 18, 2026

26

Ep. 3335 - Q&A: “What separates small earners from big ones?”

5:29 Feb 17, 2026

27

Ep. 3334 - First $1,000: “I started by setting up a booth at the farmer's market…”

5:05 Feb 16, 2026

28

Ep. 3333 - STORY: Game of Cones: Two Women Make Architecturally-Inspired Ice Cream

7:26 Feb 15, 2026

29

Ep. 3332 - Q&A: “How to sell a reusable fork…”

4:57 Feb 14, 2026

30

Ep. 3331 - STORY: Dog Stocking Hustle Earns Husky Payoff

8:02 Feb 13, 2026

31

Ep. 3330 - TBT: The Accountant Who Sold Spreadsheets to Etsy Sellers

8:31 Feb 12, 2026

32

Ep. 3329 - Q&A: “Should I pay a publicist to book me as a podcast guest?”

4:25 Feb 11, 2026

33

Ep. 3328 - Q&A: “Why do online courses cost so much—or so little?”

5:05 Feb 10, 2026

34

Ep. 3327 - First $1,000: “I dropped off hundreds of orders at the post office…”

4:50 Feb 9, 2026

35

Ep. 3326 - STORY: Inventor Unclogs Profits With Innovative Drain Solution

7:51 Feb 8, 2026

36

Ep. 3325 - Q&A: “How can I become a personal finance influencer?”

5:04 Feb 7, 2026

37

Ep. 3324 - Failure Friday: “My virtual assistant was a fan of quiet quitting…”

5:54 Feb 6, 2026

38

Ep. 3323 - TBT: English Language Game Throws Down Amazon Gauntlet

7:24 Feb 5, 2026

39

Ep. 3322 - Q&A: “Can I import rain barrels from the Netherlands?”

4:26 Feb 4, 2026

40

Ep. 3321 - Q&A: “Should I start a new business or expand my current one?”

5:04 Feb 3, 2026

41

Ep. 3320 - First $1,000: Michigan Accountant Moonlights as Engagement Photographer

5:39 Feb 2, 2026

42

Ep. 3319 - STORY: Physician Designs Plush Toys to Teach Anatomy

6:56 Feb 1, 2026

43

Ep. 3318 - Q&A: “How can I sell on a platform like NextDoor?”

4:13 Jan 31, 2026

44

Ep. 3317 - STORY: Jiu-Jitsu Instructor Pins Down Mobile Workout Tool

7:10 Jan 30, 2026

45

Ep. 3316 - TBT: Designer Scales Personalized Wedding Products to $1M+

6:10 Jan 29, 2026

46

Ep. 3315 - Q&A: “How do I transition from Etsy to Shopify?”

4:49 Jan 28, 2026

47

Ep. 3314 - Q&A: “What's the best software to write a non-fiction book?”

4:33 Jan 27, 2026

48

Ep. 3313 - First $1,000: “I still remember the day I hit the goal…”

7:45 Jan 26, 2026

49

Ep. 3312 - STORY: The Clothes Dryer That Changed a Family Forever

7:53 Jan 25, 2026

50

Ep. 3311 - Q&A: “Get paid to help brands with their Terms & Conditions?”

4:38 Jan 24, 2026

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