Best Chris & Jolie Guillebeau Podcasts (2025)

1
Weekend Workshop: The “Never Boss” Philosophy 5:33

1d ago5:33

5:33

#block-a19db227 h2 { width: 401px; } What It’s About A “company of one” proves you can build a thriving business without bosses—or employees. Notes from Chris Episode 3263 It’s Weekend Workshop, and it’s new! Listen to today’s episode to learn more… SEE ALSO: Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the who…

1
Q&A: “Should I raise my coaching rates or add more clients?” 7:33

2d ago7:33

7:33

#block-1c2afe1b h2 { width: 401px; } What It’s About Will a modest rate bump outrun the hustle of adding more clients? Notes from Chris Episode 3262 Service businesses hit a hard ceiling: a week only holds so many billable hours. When the calendar is close to full, growth comes down to choosing the right lever—charge a bit more or squeeze in more s…

1
Q&A: “Is my struggling side hustle worth saving?” 6:21

3d ago6:21

6:21

#block-b04a8b87 h2 { width: 401px; } What It’s About Is a slow-starting side hustle a normal lull or a sign to pivot? Notes from Chris Episode 3261 Not every side hustle explodes. Many take a year to stabilize. But eight months of nightly effort for only six hundred dollars is a signal that something—pricing, product, marketing, or audience—isn’t w…

1
TBT: This Tiny Tool Earns Thousands Every Election Season 7:01

5d ago7:01

7:01

#block-37bc616f h2 { width: 401px; } What It’s About A part-time coder turns a simple canvassing scheduler into a paid election-season tool. Notes from Chris Episode 3260 Welcome to Throwback Thursday, where we take an in-depth look at someone who’s story has evolved considerably since we first featured them. Last week, we heard how a creative proj…

1
Accountant Earns Six-Figures Selling Spreadsheets to Etsy Sellers 5:29

6d ago5:29

5:29

#block-ab8bffcd h2 { width: 401px; } What It’s About A burned-out CPA turns spreadsheet templates into a six-figure Etsy business. Notes from Chris Episode 3259 In today’s story… ..A dissatisfied accountant longs to do something different, so at first she begins selling handmade items on Etsy. Nothing wrong with that, but then she finds a way to do…

1
Q&A: “Can I profit from flipping open-box customer returns? 6:21

7d ago6:21

6:21

#block-6d4452e4 h2 { width: 401px; } What It’s About Are open-box deals a smart resale play or a reseller trap? Notes from Chris Episode 3258 Returns and open-box items are a hidden supply chain. Retailers and Amazon sellers unload mixed-condition goods to liquidators who sell them by the pallet. Some resellers make healthy margins; others buy myst…

1
First $1,000: DIY Headshot Stations for University Job Fairs 6:32

8d ago6:32

6:32

#block-eaa08cc1 h2 { width: 401px; } What It’s About A portable headshot station turns an old iPad into a profitable campus rental. Notes from Chris Episode 3257 Today’s episode is part of a feature we call ‘Your First $1,000.’ As you might surmise from the title, this is all about how someone made their first $1,000. How did they get to that point…

1
Weekend Workshop: Building Teams Without Hiring Employees 7:11

9d ago7:11

7:11

#block-8d663556 h2 { width: 401px; } What It’s About A laid-off mom turned a simple transcription service into a scalable business run by contractors. Notes from Chris Episode 3256 It’s Weekend Workshop, and it’s new! Listen to today’s episode to learn more… SEE ALSO: Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gai…

1
Q&A: “When is uneven side-hustle income safe to rely on?” 7:18

10d ago7:18

7:18

#block-b8e8e48f h2 { width: 401px; } What It’s About When can a side hustle with wild revenue swings safely replace a steady paycheck? Notes from Chris Episode 3255 Side-hustle math can be deceptive: average revenue says “go!” while monthly swings says “wait!” Bills arrive on a fixed schedule, but craft sales follow seasons. The goal isn’t just rep…

Podcasts Worth a Listen

Chris & Jolie Guillebeau Podcasts

Podcasts Worth a Listen

1
Side Hustle School

Chris Guillebeau

1
Weekend Workshop: The “Never Boss” Philosophy 5:33

1
Q&A: “Should I raise my coaching rates or add more clients?” 7:33

1
Q&A: “Is my struggling side hustle worth saving?” 6:21

1
TBT: This Tiny Tool Earns Thousands Every Election Season 7:01

1
Accountant Earns Six-Figures Selling Spreadsheets to Etsy Sellers 5:29

1
Q&A: “Can I profit from flipping open-box customer returns? 6:21

1
First $1,000: DIY Headshot Stations for University Job Fairs 6:32

1
Weekend Workshop: Building Teams Without Hiring Employees 7:11

1
Q&A: “When is uneven side-hustle income safe to rely on?” 7:18

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