Chris Guillebeau

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. Hosted on Acast. See acast.com/privacy for more information.

Be sure to visit the podcast's website and support the creator: sidehustleschool.com

Author

Chris Guillebeau

Category

Business

Podcast website

sidehustleschool.com

Latest episode

Oct 26, 2026

Where to listen?

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Episodes

Ep. 2964 - Q&A: “How can I build trust in a tax service for digital nomads?” 11.02.2025

In today's episode, we help an accountant build trust with digital nomads and scale her international tax service. Learn how to establish credibility, stay on top of regulations, and grow with confidence. 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 an...

Ep. 2963 - First $1,000: London Underground Photo Safaris 10.02.2025

In this week's First $1,000 segment, we hear from a London photographer who created urban photo safaris for tourists. Learn how they combined hidden gems and photography lessons to get booked over and over. 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...

Ep. 2962 - Weekend Workshop: Become a Side Hustle Detective 09.02.2025

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: learning from others' success. 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,...

Ep. 2961 - Q&A: “What’s the best way to pre-sell a product I haven’t made yet?” 08.02.2025

Can you sell a product that doesn't fully exist yet? In this episode, we help an engineer navigate the world of pre-sales, with tips on how to test demand while building trust with potential customers. 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 l...

Ep. 2960 - Q&A: “How to price your services without undervaluing your expertise?” 07.02.2025

In today's episode, we help a fitness trainer navigate the tricky balance of pricing her postpartum workout plans. Learn how to offer options for different budgets and build a sustainable business—while staying true to your mission. 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...

Ep. 2959 - TBT: Personalized Travel Itineraries for Digital Nomads 06.02.2025

In this week's Throwback Thursday segment, discover how a travel lover in Lisbon began crafting personalized itineraries for remote workers, helping them find coworking gems and local culture—while earning a solid income. 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...

Ep. 2958 - STORY: Florida Man Leads Scooter Tours After Watching Macklemore Video 05.02.2025

Had a broken keyboard, bought a broken keyboard: this corporate refugee relocates to Florida and kicks off a new hustle leading adult scooter tours. 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. Show notes: S...

Ep. 2957 - Q&A: “How can I make a slow month more productive?” 04.02.2025

In this episode, we explore ways to make quiet months productive, from learning new skills to preparing for a strong comeback. What can you do during a slow season in your 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 listener Q&...

Ep. 2956 - First $1,000: Temporary Tattoo Artist for Events 03.02.2025

In this week's First $1,000 segment, we explore how a Mississippi artist turned their love of design into a thriving event business, offering custom temporary tattoos for weddings, parties, and corporate events. 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...

Ep. 2955 - Weekend Workshop: Choosing Your Best Idea 02.02.2025

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: choosing your best idea. 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 s...

Ep. 2954 - Q&A: “Is a subscription box for indie comics the right idea?” 01.02.2025

In today's episode, we help a comic enthusiast decide whether a subscription box is the best way to promote indie creators. Learn about alternative models that are more flexible, cost-effective, and easier to manage. 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 guide...

Ep. 2953 - Q&A: “How can I negotiate better terms with my suppliers?” 31.01.2025

In today's episode, we help a bakery owner navigate supplier negotiations. Learn how to improve payment terms, reduce costs, and build stronger partnerships with your vendors. 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 da...

Ep. 2952 - TBT: Microbrewery Tours Expand to Hops and Brewing Classes 30.01.2025

In this week's Throwback Thursday segment, we explore how a microbrewery tour guide in Chicago turned their passion for craft beer into a hands-on 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 listener Q&A several days each week. Show...

Ep. 2951 - Lifelong Girl Scout Earns Her Side Hustle Badge 29.01.2025

Jodi Carlson devoted much of her adult life to Girl Scout troops—and eventually turned it into the side hustle of her dreams. 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. Show notes: SideHustleSchool.c...

Ep. 2950 - Q&A: “How much time should I spend on social media each week?” 28.01.2025

In today's episode, we help a handmade pottery business owner decide how much time to spend on social media each week. Learn how to focus on what works, save time, and grow your online presence without burnout. 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 less...

Ep. 2949 - First $1,000: Career Transition Guides Quickly Earn $25,000 27.01.2025

In this week's First $1,000 segment, we meet a former HR professional who built a side hustle creating career transition guides. She shares how niche guides and live workshops helped her hit $1,000 and scale her business for consistent 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,...

Ep. 2948 - Weekend Workshop: Money Math Made Simple 26.01.2025

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: making smart (and simple!) projections. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. T...

Ep. 2947 - Q&A: “What’s the best way to offer payment plans?” 25.01.2025

In today's episode, we help an online course creator set up payment plans that attract customers while minimizing risks. Learn the best strategies to balance accessibility and profitability. 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...

Ep. 2946 - Q&A: “When should I hire a virtual assistant?” 24.01.2025

In today's episode, we help a side hustler decide if it's time to hire a virtual assistant. Learn how to assess your readiness, find the right help, and delegate tasks effectively without breaking the bank. 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...

Ep. 2945 - TBT: Bringing STEM to Life with Custom Science Kits 23.01.2025

In this week's Throwback Thursday segment, we hear how a San Jose educator scaled their DIY science kits. Learn how school partnerships and workshops helped them deliver hands-on STEM experiences to hundreds of kids every 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 include...

Ep. 2944 - The $300,000 Bouncy Castle Drop-Shipping Hustle 22.01.2025

A Texas man puts a bounce in his step by finding a uniquely profitable niche. This bouncy hustle earns multiple six-figures in its first year! 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. Show notes: SideHus...

Ep. 2943 - Q&A: “Should I create a niche blog or a broader one?” 21.01.2025

In today's episode, we help a new blogger decide whether to focus on a specific niche or go broad to grow faster. Learn why starting small and specific can give you the best chance for success. 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...

Ep. 2942 - First $1,000: Turning Central Park Picnics into Profits 20.01.2025

In this week's First $1,000 segment, we hear from an NYC event planner who started a pop-up picnic service in the city's parks. Learn how she marketed her picnics and reached her first $1,000. 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...

Ep. 2941 - Weekend Workshop: Sizing Up Your Ideas 19.01.2025

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: sizing up your ideas. 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...

Ep. 2940 - Q&A: “Is a 40% commission worth it for my business?” 18.01.2025

In today's episode, we help a jewelry maker decide whether to keep selling in a local shop that takes a 40% commission. We'll explore the pros and cons, negotiation tips, and how to maintain strong relationships while growing your 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...

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