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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. 3082 - First $1,000: Partners Turn Neglected Washers into Solid Profit

6 mins; June 09, 2025

Ep. 3081 - Weekend Workshop: Grow What Works, Let Go of What Doesn't

7 mins; June 08, 2025

Ep. 3080 - Q&A: “Should you fight unfair refund requests or just move on?”

4 mins; June 07, 2025

Ep. 3079 - Q&A: “How do I get featured in holiday gift guides?”

5 mins; June 06, 2025

Ep. 3078 - TBT: How ‘Pinspiration’ Became a Full-Time Hustle

7 mins; June 05, 2025

Ep. 3077 - STORY: Four Friends Create Conversations, Earn $400,000 in 8 Months

7 mins; June 04, 2025

Ep. 3076 - Q&A: “Should I add a live chat feature to my website?”

4 mins; June 03, 2025

Ep. 3075 - First $1,000: Marketing Pro Builds GPT Bots—No Code Needed

5 mins; June 02, 2025

Ep. 3074 - Weekend Workshop: Measure What Matters

8 mins; June 01, 2025

Ep. 3073 - Q&A: “What’s the purpose of more than one business bank account?”

5 mins; May 31, 2025

Ep. 3072 - Q&A: “Why do struggling businesses keep their doors open?”

4 mins; May 30, 2025

Ep. 3071 - TBT: From DIY Pet Tributes to Six-Figure Etsy Shop

5 mins; May 29, 2025

Ep. 3070 - STORY: High School Student Earns $20,000 Making Wooden Bow Ties

6 mins; May 28, 2025

Ep. 3069 - Q&A: “I’m ready to sell my side hustle—how do I do it?”

5 mins; May 27, 2025

Ep. 3068 -First $1,000: Real Estate Office Rents Out Podcast Studio

5 mins; May 26, 2025

Ep. 3067 - Weekend Workshop: Frame Your First Dollar

6 mins; May 25, 2025

Ep. 3066 - Q&A: “Is YouTube really ‘top of funnel’ for educational creators?”

5 mins; May 24, 2025

Ep. 3065 - Q&A: “How do I take a break from my hustle without losing momentum?”

5 mins; May 23, 2025

Ep. 3064 - TBT: Turning Plastic into High-End Interior Pieces

5 mins; May 22, 2025

Ep. 3063 - STORY: Golfer Takes Swing At Content Website

8 mins; May 21, 2025

Ep. 3062 - Q&A: “Are there any ‘good’ MLMs?”

4 mins; May 20, 2025

Ep. 3061 -First $1,000: Coffee Gear Affiliate Site Brews Profits

7 mins; May 19, 2025

Ep. 3060 - Weekend Workshop: Burn Down the Furniture Store

6 mins; May 18, 2025

Ep. 3059 - Q&A: “How can I wireframe a website?”

4 mins; May 17, 2025

Ep. 3058 - Q&A: “Is it a good time to launch a meme coin?”

5 mins; May 16, 2025

Ep. 3057 -TBT: Crossing Borders, Boosting Orders

7 mins; May 15, 2025

Ep. 3056 - STORY: Architect Creates Mini-Blind Repair Too

8 mins; May 14, 2025

Ep. 3055 - Q&A: “Can you really publish a book in a week?”

5 mins; May 13, 2025

Ep. 3054 - First $1,000: Community Host Boosts Engagement and Retention

5 mins; May 12, 2025

Ep. 3053 - Weekend Workshop: Test, Test, and Test Again

6 mins; May 11, 2025

Ep. 3052 - Q&A: “How can I push past hesitation and market my creative work?”

5 mins; May 10, 2025

Ep. 3051 - Q&A: “How do I balance what I love with what the market wants?”

4 mins; May 09, 2025

Ep. 3050 - TBT: Lawn Sign Biz Expands to Wedding Décor Rentals

5 mins; May 08, 2025

Ep. 3049 - STORY: Internet Trolls Eat Their Words In This Comedic Cake Hustle

7 mins; May 07, 2025

Ep. 3048 - Q&A: “Best practices for Meta ads?”

4 mins; May 06, 2025

Ep. 3047 - First $1,000: Pop-Up Cosplay Salon Takes Con-Goers by Surprise

6 mins; May 05, 2025

Ep. 3046 - Weekend Workshop: Ask 10 People for Help

6 mins; May 04, 2025

Ep. 3045 - Q&A: “Should I switch my business to a subscription model?”

5 mins; May 03, 2025

Ep. 3044 - Q&A: “Why do authors offer pre-order bonuses?”

5 mins; May 02, 2025

Ep. 3043 - TBT: From Cracked Screens to Tech Buyback Business

5 mins; May 01, 2025

Ep. 3042 - STORY: Fashion Buyer Creates Quirky Comfort Craze

6 mins; April 30, 2025

Ep. 3041 - Q&A: “Should I expand the services I offer?”

4 mins; April 29, 2025

Ep. 3040 - First $1,000: Flipping Phones and Tablets for Fun and Profit

5 mins; April 28, 2025

Ep. 3039 - Weekend Workshop: Sell Like a Girl Scout

5 mins; April 27, 2025

Ep. 3038 - Q&A: “When is it worth spending money on your side hustle?”

5 mins; April 26, 2025

Ep. 3037 - Q&A: “How do I turn being an industry outsider into an advantage?”

4 mins; April 25, 2025

Ep. 3036 - TBT: Montana Videographer Redefines Remote Filming

6 mins; April 24, 2025

Ep. 3035 - STORY: Frozen Yogurt Dog Treats Are No Barking Matter

6 mins; April 23, 2025

Ep. 3034 - Q&A: “How can I incorporate activism into my brand without seeming performative?”

4 mins; April 22, 2025

Ep. 3033 - First $1,000: Feeding the Neighborhood, One Block at a Time

6 mins; April 21, 2025

Ep. 3032 - Weekend Workshop: Launch Before You’re Ready

6 mins; April 20, 2025

Ep. 3031 - Q&A: “How do I create and sell a premium online course?”

4 mins; April 19, 2025

Ep. 3030 - Q&A: “How do I prepare for tech failures without overloading my setup?”

5 mins; April 18, 2025

Ep. 3029 - TBT: Travel Blog Becomes Spring Break Powerhouse

6 mins; April 17, 2025

Ep. 3028 - STORY: College Student Hacks Into $40,000 A Month Side Hustle

7 mins; April 16, 2025

Ep. 3027 - Q&A: “How do side hustle ‘power laws’ work?”

5 mins; April 15, 2025

Ep. 3026 - First $1,000: From Text Messages to Digital Concierge

5 mins; April 14, 2025

Ep. 3025 - Weekend Workshop: Making Time for What Matters

6 mins; April 13, 2025

Ep. 3024 - Q&A: “What’s the ROI of renting out equipment or tools?”

4 mins; April 12, 2025

Ep. 3023 - Q&A: “Could selling templates for AI tools be a business?”

4 mins; April 11, 2025

Ep. 3022 - TBT: When Selling Prints Wasn’t Enough

5 mins; April 10, 2025

Ep. 3021 - STORY: Immigrant Couple Translates Heritage Into Children’s Flash Cards

7 mins; April 09, 2025

Ep. 3020 - Q&A: “How do I manage last-minute requests without burning out?”

5 mins; April 08, 2025

Ep. 3019 - First $1,000: Miami Divorce Planner Offers “Freedom Celebrations”

6 mins; April 07, 2025

Ep. 3018 - Weekend Workshop: Design Your First Workflow

6 mins; April 06, 2025

Ep. 3017 - Q&A: “How do I balance transparency with professionalism?”

4 mins; April 05, 2025

Ep. 3016 - Q&A: “Is there still room to start a podcast in 2025?”

4 mins; April 04, 2025

Ep. 3015 - TBT: Bringing Tokyo’s Best Stationery to Global Audiences

6 mins; April 03, 2025

Ep. 3014 - STORY: Accountant Earns $233,751 Reselling Items He Buys at Walmart

8 mins; April 02, 2025

Ep. 3013 - Q&A: “How do I find my first clients without paid advertising?”

5 mins; April 01, 2025

Ep. 3012 - First $1,000: Stay-at-Home Dad’s Virtual Garage Sale Venture

4 mins; March 31, 2025

Ep. 3011 - Weekend Workshop: Make It Easy to Get Paid

8 mins; March 30, 2025

Ep. 3010 - Q&A: “How to set better boundaries with clients?”

5 mins; March 29, 2025

Ep. 3009 - Q&A: “How can I work fewer hours without losing income?”

5 mins; March 28, 2025

Ep. 3008 - TBT: Pet Furniture Maker Adds Digital Blueprints for DIYers

6 mins; March 27, 2025

Ep. 3007 - STORY: Florida Woman Gets Paid to Remove Poisonous Frogs

7 mins; March 26, 2025

Ep. 3006 - Q&A: “How do I set the right hourly rate for my side hustle?”

4 mins; March 25, 2025

Ep. 3005 - First $1,000: This “Crypto Tax Whisperer” Takes On the IRS

5 mins; March 24, 2025

Ep. 3004 - Weekend Workshop: Create a Side Hustle Shopping List

7 mins; March 23, 2025

Ep. 3003 - Q&A: “How can I get clients to provide more accurate information?”

4 mins; March 22, 2025

Ep. 3002 - Q&A: “How can I stand out in a world of AI-generated content?”

5 mins; March 21, 2025

Ep. 3001 - TBT: Food Blog Grows to Thriving Culinary Ecosystem

6 mins; March 20, 2025

Ep. 3000 - STORY: “Pocket Monkey” Tool Sells 500,000 Units

7 mins; March 19, 2025

Ep. 2999 - Q&A: “How to prioritize tasks and to-do items without getting overwhelmed?”

5 mins; March 18, 2025

Ep. 2998 - First $1,000: From Malibu Bartender to At-Home Bar Designer

5 mins; March 17, 2025

Ep. 2997 - Weekend Workshop: Finding the Right Price

6 mins; March 16, 2025

Ep. 2996 - Q&A: “Can I legally sell t-shirts with retro images of celebrities?”

4 mins; March 15, 2025

Ep. 2995 - Q&A: “How to organize leads without getting overwhelmed?”

5 mins; March 14, 2025

Ep. 2994 - TBT: Streamlining Standardized Test Preparation

7 mins; March 13, 2025

Ep. 2993 - STORY: Homemade Art Tutorials Turn Struggling Artist Into YouTube Star

7 mins; March 12, 2025

Ep. 2992 - Q&A: “How do I handle indecisive event planning clients?”

5 mins; March 11, 2025

Ep. 2991 - First $1,000: My Life as a Proposal Planner

4 mins; March 10, 2025

Ep. 2990 - Weekend Workshop: Assemble the Nuts and Bolts

7 mins; March 09, 2025

Ep. 2989 - Q&A: “What should I do if a brand uses my photo without permission?”

5 mins; March 08, 2025

Ep. 2988 - Q&A: “How do I create passive income from a skill-based service?”

5 mins; March 07, 2025

Ep. 2987 - TBT: Solo Nutrition Practice Offers Corporate Wellness Service

6 mins; March 06, 2025

Ep. 2986 - STORY: Itchy Honeymoon Shaves Way To Pubic Oil Kingdom

8 mins; March 05, 2025

Ep. 2985 - Q&A: “How can I relaunch a product that didn’t sell well the first time?”

5 mins; March 04, 2025

Ep. 2984 - First $1,000: Hitting the Highway for RV Deliveries

5 mins; March 03, 2025

Ep. 2983 - Weekend Workshop: Create an Origins Story

6 mins; March 02, 2025

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