Best Chris Guillebeau / Onward Project Podcasts (2025)

1
Ep. 3264 - First $1,000: Flipping Rolling Carts & Filing Cabinets 6:43

Play Pause

5h ago6:43

6:43

In this week’s First $1,000 segment, dull beige cabinets became hot pastel storage after one coat of paint and the right Facebook group. In just nineteen days, that makeover hustle rolled past a thousand dollars in profit—no moving truck required. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ear…

1
Ep. 3263 - Weekend Workshop: The Never Boss Philosophy 8:14

1d ago8:14

8:14

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: “never have a boss, never be a boss.” Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn…

1
Ep. 3262 - Q&A: “Should I raise my coaching rates or add more clients?” 5:15

2d ago5:15

5:15

Today’s caller has two levers—charge a bit more or work a bit more. We’ll test both in plain numbers, then show why nudging the price usually wins for a solo coach. 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 …

1
Ep. 3261 - Q&A: “Is my struggling side hustle worth saving?” 5:49

3d ago5:49

5:49

A listener wants to know if a slow start is normal, or a warning sign that another business might be better. We’ll set a simple 90-day experiment to decide whether to double down, redesign, or walk away. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Th…

1
Ep. 3260 - TBT: Campaign Scheduling Tool Turns Out Voters 5:21

4d ago5:21

5:21

In this week’s Throwback Thursday segment, find out how a small campaign tool turned into a software product now licensed by multiple counties. 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 …

1
Ep. 3259 - STORY: Accountant Earns Six-Figures Selling Spreadsheets to Etsy Sellers 7:38

5d ago7:38

7:38

She was burned out being a CPA, so she turned her efforts to an Etsy business—but it wasn’t long before she was hitting the books again, just in a more creative way. Her new spreadsheets help Etsy sellers and earn a six-figure income for her. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ext…

1
Ep. 3258 - Q&A: “Can I profit from flipping open-box customer returns?” 4:59

6d ago4:59

4:59

Today’s listener wants to turn store returns into cash. We’ll cover how to evaluate a pallet, estimate true margins, and avoid getting stuck with dead inventory. 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 les…

1
Ep. 3257 - First $1,000: DIY Headshot Stations for University Job Fairs 5:35

7d ago5:35

5:35

In this week’s First $1,000 segment, campus recruiters needed polished LinkedIn photos—but photographers were booked solid. One creative grad built a plug-and-play headshot booth, rented it four times in a month, and snapped up his first grand without clicking the shutter himself. Side Hustle School features a new episode EVERY DAY, featuring detai…

1
Ep. 3256 - Weekend Workshop: Building Teams Without Hiring Employees 7:51

8d ago7:51

7:51

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: a small-scale, large-reach transcription business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of pe…

1
Ep. 3255 - Q&A: “When is uneven side-hustle income safe to rely on?” 4:44

9d ago4:44

4:44

Today’s caller makes more money on weekends than at the day job—but their revenue graph looks like a heart monitor. Can they rely enough on their extra income to go all-in? 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…

1
Ep. 3254 - Q&A: “How do I price my VA work for true value?” 4:31

10d ago4:31

4:31

If clients praise your speed but you’re still billing like a beginner, it’s time to level up. Today we pinpoint the three value levers that justify higher VA rates—and a script that keeps loyal 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…

1
Ep. 3253 - TBT: Scarce Lego Sets Build Value Over Time 6:18

11d ago6:18

6:18

In this week’s Throwback Thursday segment, find out how one patient side hustler stockpiled retired LEGO sets, held them like collectibles, and eventually parlayed the profits into a full-on store. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This yea…

1
Ep. 3252 - STORY: Frenchman Says Bonjour to $35,000/Month Foodie Hustle 8:02

12d ago8:02

8:02

After relocating to Quebec, this continental creative brings seasonal flavor to an artisanal food retailing biz. 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. Sho…

1
Ep. 3251 - Q&A: “Is my burnout a signal to pivot?” 5:13

13d ago5:13

5:13

Are you just tired—or do you need a bigger break? In this episode, we’ll help a listener take a stress-test to know if they need rest, a redesign, or a full business pivot. 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…

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

14d 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&…

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

15d 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…

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

16d 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…

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

17d 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…

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

18d 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, …

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

19d 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…

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

20d 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…

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

21d 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 …

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

22d 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…

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

23d 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…

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

24d 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…