Best Chris Guillebeau Onward Project Podcasts (2025)

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Ep. 3250 - First $1,000: Digital Window Menu Boards for Food Trucks 6:00

Play Pause

16h ago6:00

6:00

In this week’s First $1,000 segment, a designer helps food trucks and pop-up restaurants get rid of chalk dust and update to the digital age. 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&…

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Ep. 3249 - Weekend Workshop: From Ski Bum to Six-Figure Teacher 7:07

1d ago7:07

7:07

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: an online snow-skiing school. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra m…

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Ep. 3248 - Q&A: “Should I spend $2,000 on retention or acquisition?” 5:18

3d ago5:18

5:18

Today’s caller runs a tiny subscription app and has two grand to spend. Should that money patch cancelations or chase new sign-ups? We’ll do the napkin math and land on a clear next step. 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 sho…

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Ep. 3247 - Q&A: “Instagram, TikTok, or LinkedIn—how do I choose?” 5:25

4d ago5:25

5:25

Posting everywhere spreads you thin; posting in the right place compounds momentum. Today we break down a three-question filter that shows exactly where this side hustler’s wallets should live first. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This y…

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Ep. 3246 - TBT: Recruiters Pay Me to Tear Apart Their Emails 5:38

5d ago5:38

5:38

In this week’s Throwback Thursday segment, hear how one copy-savvy side hustler turned a collection of recruiter emails into a paid “swipe file,” and then built a monthly subscription around it. 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, …

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Ep. 3245 - STORY: Six-Figure Beekeeping Biz Buzzes for Minnesota Couple 6:49

6d ago6:49

6:49

The buzzworthy journey of Minnesotan bees and their keepers. These hardy bees don’t mess around—last year they produced $150,000 in sweet profits. 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 listen…

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Ep. 3244 - Q&A: “How do I upsell without sounding pushy?” 4:26

7d ago4:26

4:26

Great contracting work often reveals the next problem to solve. Here’s a simple script that turns an “upsell” into an obvious win for the client—and leaves everyone feeling good about the extra invoice. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Thi…

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Ep. 3243 - First $1,000: Cozy Reading Gadget Turns Pages and Profit 6:20

8d ago6:20

6:20

A bedtime-reading addict bend a paperclip into a page holder, refines it into a soft-touch clip, and flips his ledger from red ink to a four-figure win. 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 …

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Ep. 3242 - Weekend Workshop: “Digital Documentation” Earns Passive Income 8:08

9d ago8:08

8:08

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: how a single PDF guide earned $120,000 in its first year. Side Hustle School features a new episode EVERY DAY, featuring detailed case studie…

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Ep. 3241 - Q&A: “Is remote-worker visa consulting a real business?” 6:05

10d ago6:05

6:05

Remote-worker visas are booming—and bewildering. Today we price a “visa concierge,” unpack simple liability safeguards, and gauge whether the market can pay more than pocket change. 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 incl…

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Ep. 3240 - Q&A: “Should I tell my clients I’m using AI?” 5:22

11d ago5:22

5:22

AI tools can double your output, but not everyone’s comfortable with it. Today we map a three-part policy for disclosing AI use that keeps trust high, quality higher, and clients on board. 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 sh…

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Ep. 3239 - TBT: This Tiny Spreadsheet Tool Pays the Rent 6:00

12d ago6:00

6:00

In this week’s Throwback Thursday segment, meet a side hustler who built a simple browser-based spreadsheet tool. It earns enough to cover his rent each 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 lesso…

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Ep. 3238 - STORY: Agricultural Teacher Earns $200,000 Selling Lesson Plans 7:25

13d ago7:25

7:25

After creating course materials for a forgotten group of educators, this agricultural teacher now earns a significant income from a growing 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 lis…

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Ep. 3237 - Q&A: “Will professionals trade hours instead of cash?” 4:41

14d ago4:41

4:41

Can busy side hustlers trade skills instead of dollars? Today we outline a lean time-bank model—simple rules, low overhead, and real incentives to keep everyone honest. 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 gui…

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Ep. 3236 - First $1,000: Turning Cable Chaos into Magnetic Profit 5:58

15d ago5:58

5:58

Tired of cables dangling each time your standing desk rises? A quick TikTok clip of magnetic rails snapping cords into place sparked a rush of orders for this savvy side hustler. 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 include…

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Ep. 3235 - Weekend Workshop: The Wandering Teacher's Global Classroom 8:15

16d ago8:15

8:15

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: an early language hacker starts “Fluent in 3 Months.” Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of…

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Ep. 3234 - Q&A: “What’s a fair founder-investor deal between friends?” 5:35

17d ago5:35

5:35

Cash can launch the product; labor will keep it alive. Today we map out founder-friendly splits, vesting schedules, and a simple “dynamic equity” formula that grows with effort. 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…

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Ep. 3233 - Q&A: “Where do I find my first paying customer?” 4:56

18d ago4:56

4:56

One sale beats a hundred compliments. Let’s walk through a low-risk, weekend-ready plan that puts money in this side hustler’s hands within two weeks. 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 li…

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Ep. 3232 - TBT: The Garage Gym Hustle That Went Digital 6:00

19d ago6:00

6:00

In this week’s Throwback Thursday segment, learn how one fitness fan turned flipping gym equipment into a small media business. He now sells setup guides and curates weekly home gym deals for thousands of subscribers. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting…

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Ep. 3231 - STORY: The Coffee Grinder That Made $300,000 8:25

20d ago8:25

8:25

Rise and shine! A petroleum engineer finds the perfect item to resell on Amazon. He goes on to sell $300,000 worth of the humble coffee grinder. 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…

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Ep. 3230 - Q&A: “How do I test Facebook vs. free traffic?” 5:22

21d ago5:22

5:22

Free traffic feels safe, but paid ads might unlock a faster lane—IF the math checks out. Let’s design a two-week, $200 ad test with clear “go / no-go” numbers so this side hustler can see truth, not guesswork. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their j…

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Ep. 3229 - First $1,000: Shopify Library Becomes Paid Subscription 6:45

22d ago6:45

6:45

Shopify merchants kept begging forums for the same quick theme fixes. One developer bundled all his proven snippets behind a $15 monthly paywall—and 170 store owners are happily copying, pasting, and paying. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job…

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Ep. 3228 - Weekend Workshop: When Getting Fired Becomes Your Best Break 7:15

23d ago7:15

7:15

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: if he hadn’t been pushed, he wouldn’t have made the leap. Side Hustle School features a new episode EVERY DAY, featuring detailed case studie…

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Ep. 3227 - Q&A: “Why won’t TikTok followers join my newsletter?” 5:19

24d ago5:19

5:19

TikTok, Snap, and Instagram fame is fun, but e-mail tends to pay the bills. Today we lay out the follower-to-inbox conversion math, including the moment a list becomes non-negotiable. 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 in…

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Ep. 3226 - Q&A: “Can I legally profit from salvaging barn wood?” 5:03

25d ago5:03

5:03

Old barns can be gold mines—or legal landmines. Today we cover permits, insurance, and realistic margins for turning reclaimed boards into profit. 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 listen…

Chris Guillebeau Onward Project Podcasts

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Side Hustle School

Chris Guillebeau / Onward Project

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Ep. 3250 - First $1,000: Digital Window Menu Boards for Food Trucks 6:00

1
Ep. 3249 - Weekend Workshop: From Ski Bum to Six-Figure Teacher 7:07

1
Ep. 3248 - Q&A: “Should I spend $2,000 on retention or acquisition?” 5:18

1
Ep. 3247 - Q&A: “Instagram, TikTok, or LinkedIn—how do I choose?” 5:25

1
Ep. 3246 - TBT: Recruiters Pay Me to Tear Apart Their Emails 5:38

1
Ep. 3245 - STORY: Six-Figure Beekeeping Biz Buzzes for Minnesota Couple 6:49

1
Ep. 3244 - Q&A: “How do I upsell without sounding pushy?” 4:26

1
Ep. 3243 - First $1,000: Cozy Reading Gadget Turns Pages and Profit 6:20

1
Ep. 3242 - Weekend Workshop: “Digital Documentation” Earns Passive Income 8:08

1
Ep. 3241 - Q&A: “Is remote-worker visa consulting a real business?” 6:05

1
Ep. 3240 - Q&A: “Should I tell my clients I’m using AI?” 5:22

1
Ep. 3239 - TBT: This Tiny Spreadsheet Tool Pays the Rent 6:00

1
Ep. 3238 - STORY: Agricultural Teacher Earns $200,000 Selling Lesson Plans 7:25

1
Ep. 3237 - Q&A: “Will professionals trade hours instead of cash?” 4:41

1
Ep. 3236 - First $1,000: Turning Cable Chaos into Magnetic Profit 5:58

1
Ep. 3235 - Weekend Workshop: The Wandering Teacher's Global Classroom 8:15

1
Ep. 3234 - Q&A: “What’s a fair founder-investor deal between friends?” 5:35

1
Ep. 3233 - Q&A: “Where do I find my first paying customer?” 4:56

1
Ep. 3232 - TBT: The Garage Gym Hustle That Went Digital 6:00

1
Ep. 3231 - STORY: The Coffee Grinder That Made $300,000 8:25

1
Ep. 3230 - Q&A: “How do I test Facebook vs. free traffic?” 5:22

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Ep. 3229 - First $1,000: Shopify Library Becomes Paid Subscription 6:45

1
Ep. 3228 - Weekend Workshop: When Getting Fired Becomes Your Best Break 7:15

1
Ep. 3227 - Q&A: “Why won’t TikTok followers join my newsletter?” 5:19

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Ep. 3226 - Q&A: “Can I legally profit from salvaging barn wood?” 5:03