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Side Hustle School

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/

Ep. 3281 - TBT: After 1,700 Years, I Outsourced Christmas

6 mins; December 25, 2025

Ep. 3280 - STORY: The Rise and Fall of BirdSupplies.com

8 mins; December 24, 2025

Ep. 3279 - Q&A: “Do I have to be loud to sell my service?”

5 mins; December 23, 2025

Ep. 3278 - First $1,000: Helping Creators Migrate Course Content

6 mins; December 22, 2025

Ep. 3277 - Weekend Workshop: The Sculptor Who Thrived on Disaster

5 mins; December 21, 2025

Ep. 3276 - Q&A: “Can I I force myself to ship something every two weeks?”

4 mins; December 20, 2025

Ep. 3275 - Q&A: “How do I talk about pricing when it feels impolite?”

4 mins; December 19, 2025

Ep. 3274 - TBT: I Reverse-Engineered Google-Form Hacks

6 mins; December 18, 2025

Ep. 3273 - STORY: London Photographer Rents Camera Gear 1,100 Times

7 mins; December 17, 2025

Ep. 3272 - Q&A: “How do I avoid a bad review on my first client job?”

4 mins; December 16, 2025

Ep. 3271 - The Ski-Lodge Lost-and-Found Hustle

6 mins; December 15, 2025

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

7 mins; December 14, 2025

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

4 mins; December 13, 2025

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

5 mins; December 12, 2025

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

5 mins; December 11, 2025

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

7 mins; December 10, 2025

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

5 mins; December 09, 2025

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

6 mins; December 08, 2025

Ep. 3263 - Weekend Workshop: The Never Boss Philosophy

8 mins; December 07, 2025

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

5 mins; December 06, 2025

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

5 mins; December 05, 2025

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

5 mins; December 04, 2025

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

7 mins; December 03, 2025

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

4 mins; December 02, 2025

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

5 mins; December 01, 2025

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

7 mins; November 30, 2025

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

4 mins; November 29, 2025

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

4 mins; November 28, 2025

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

6 mins; November 27, 2025

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

8 mins; November 26, 2025

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

5 mins; November 25, 2025

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

6 mins; November 24, 2025

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

7 mins; November 23, 2025

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

5 mins; November 22, 2025

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

5 mins; November 21, 2025

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

5 mins; November 20, 2025

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

6 mins; November 19, 2025

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

4 mins; November 18, 2025

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

6 mins; November 17, 2025

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

8 mins; November 16, 2025

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

6 mins; November 15, 2025

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

5 mins; November 14, 2025

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

6 mins; November 13, 2025

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

7 mins; November 12, 2025

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

4 mins; November 11, 2025

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

5 mins; November 10, 2025

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

8 mins; November 09, 2025

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

5 mins; November 08, 2025

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

4 mins; November 07, 2025

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

6 mins; November 06, 2025

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

8 mins; November 05, 2025

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

5 mins; November 04, 2025

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

6 mins; November 03, 2025

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

7 mins; November 02, 2025

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

5 mins; November 01, 2025

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

5 mins; October 31, 2025

Ep. 3225 - TBT: A Guided Journal, a Friend in Need, and 1,000+ Sales

5 mins; October 30, 2025

Ep. 3224 - STORY: Line Chef Makes Millions Cooking Up Apron Empire

7 mins; October 29, 2025

Ep. 3223 - Q&A: “When does a logo actually matter?”

4 mins; October 28, 2025

Ep. 3222 - First $1,000: “CRM Makeovers” for Real Estate Agents

5 mins; October 27, 2025

Ep. 3221 - Weekend Workshop: The Premium Pricing Paradox

7 mins; October 26, 2025

Ep. 3220 - Q&A: “When is business coaching worth the cost?”

5 mins; October 25, 2025

Ep. 3219 - Q&A: “Can I sell carbon-offset checks to small brands?”

5 mins; October 24, 2025

Ep. 3218 - TBT: I Built a Supplement Guide People Actually Trust

5 mins; October 23, 2025

Ep. 3217 - STORY: Aussie Stretches Out with Online Store for Tall Women

7 mins; October 22, 2025

Ep. 3216 - Q&A: “How do I avoid a garage full of unsold kits?”

5 mins; October 21, 2025

Ep. 3215 - First $1,000: Board-Game Date Nights in a Café Basement

5 mins; October 20, 2025

Ep. 3214 - Weekend Workshop: From Spreadsheets to Six Figures

7 mins; October 19, 2025

Ep. 3213 - Q&A: “Can I monetize a college scholarship database?”

5 mins; October 18, 2025

Ep. 3212 - Q&A: “Will people pay for AI-optimized resumés?”

5 mins; October 17, 2025

Ep. 3211 - TBT: Built in a Weekend, Used by Thousands

5 mins; October 16, 2025

Ep. 3210 - STORY: Canadian Bidets Modernize Bathroom Life

7 mins; October 15, 2025

Ep. 3209 - Q&A: “How do I use exit pop-ups?”

4 mins; October 14, 2025

Ep. 3208 - First $1,000: Vintage Sewing Machine Rehab Workshops

5 mins; October 13, 2025

Ep. 3207 - Weekend Workshop: The Global Photography Pivot

6 mins; October 12, 2025

Ep. 3206 - Q&A: “How do I fight piracy without hurting buyers?”

4 mins; October 11, 2025

Ep. 3205 - Q&A: “How do I license calming coloring pages to wellness apps?”

4 mins; October 10, 2025

Ep. 3204 - TBT: The Secret Author Behind Your Favorite Romance Novel

5 mins; October 09, 2025

Ep. 3203 - STORY: Underwear Side Hustle Turns Into $500,000/Month Business

7 mins; October 08, 2025

Ep. 3202 - Q&A: “Can a ‘tech deals’ newsletter really make money?”

3 mins; October 07, 2025

Ep. 3201 - First $1,000: Weekend ASL Crash Courses for Hospitality Staff

4 mins; October 06, 2025

Ep. 3200 - Weekend Workshop: From Utah Piano Teacher to Digital Nomad

5 mins; October 05, 2025

Ep. 3199 - Q&A: “How do I handle a non-compete that hurts my side hustle?”

5 mins; October 04, 2025

Ep. 3198 - Q&A: “I went viral, but now I can’t meet demand!”

5 mins; October 03, 2025

Ep. 3197 - TBT: Turning Property Management Experience Into Digital Products

5 mins; October 02, 2025

Ep. 3196 - STORY: Google Employee Makes $100,000 Using Fiverr

7 mins; October 01, 2025

Ep. 3195 - Q&A: “Which passive-income model fits a consultant best?”

6 mins; September 30, 2025

Ep. 3194 - First $1,000: Marketer Sells Simple Fixes to Dental Clinics

5 mins; September 29, 2025

Ep. 3193 - Weekend Workshop: The Art of Electronics Arbitrage

8 mins; September 28, 2025

Ep. 3192 - Q&A: “How can a freelancer pay herself a stable salary?”

5 mins; September 27, 2025

Ep. 3191 - Q&A: “What KPIs should I track for my software biz?”

4 mins; September 26, 2025

Ep. 3190 - TBT: Helping Aspiring Film Professionals Get Hired

4 mins; September 25, 2025

Ep. 3189 - STORY: College Grad Shares “More than Mac & Cheese” Student Recipes

6 mins; September 24, 2025

Ep. 3188 - Q&A: “Can you run a YouTube channel with only AI voices and scripts?”

4 mins; September 23, 2025

Ep. 3187 - First $1,000: Typography Lover Turns Letters Into Revenue

5 mins; September 22, 2025

Ep. 3186 - Weekend Workshop: Design Disruption in Traditional Markets

5 mins; September 21, 2025

Ep. 3185 - Q&A: “How can I sell an Amazon-only FBA brand for top dollar?”

5 mins; September 20, 2025

Ep. 3184 - Q&A: “How can a coast-to-coast road trip pay for itself?”

4 mins; September 19, 2025

Ep. 3183 - TBT: Creator Builds Instagram Mastermind Pod

5 mins; September 18, 2025

Ep. 3182 - STORY: Personal Trainer Pumps Up Breakfast

7 mins; September 17, 2025

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