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.

Author

Chris Guillebeau

Category

Business

Podcast website

sidehustleschool.com

Latest episode

Jul 11, 2026

Where to listen?

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Episodes

Ep. 2932 - Q&A: “Should I open a second location?” 10.01.2025

    In today's episode, we help a fitness studio owner decide if it's the right time to open a second location. Learn how to evaluate your readiness, minimize risks, and expand without turning success into stress. 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 fre...

Ep. 2931 - TBT: From Gear Rentals to New Zealand Wilderness Adventures 09.01.2025

In this week's Throwback Thursday segment, we revisit a side hustler who began renting camping gear to tourists in New Zealand. Now, they organize guided wilderness expeditions for beginner adventurers, helping clients from around the world experience the great outdoors. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quit...

Ep. 2930 - Role-Play ing Pastor Rolls The Dice On $2,800/Month Hustle 08.01.2025

This pastor had been side-hustling his entire adult life and was about to burn out. Luckily a familiar podcast showed him how to save time, sell products, and turn his role playing passion into profit. 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. 2929 - Q&A: “What can I learn from my website analytics?” 07.01.2025

In today's episode, we help an online shop owner figure out what to focus on in her website analytics. Learn how to use conversion rates, bounce rates, and other key metrics to grow your e-commerce 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...

Ep. 2928 - First $1,000: Micro-Courses for Fast Learning 06.01.2025

In this week's First $1,000 segment, we hear from a Minneapolis teacher who turned her knowledge of children's stories into a series of short, actionable online courses. Robin shares how she marketed her micro-courses and earned 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...

2927 - Weekend Workshop: How to Spot a Profitable Side Hustle Idea 05.01.2025

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: learning to spot profitable 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 y...

Ep. 2926 - Q&A: “Is it wise to offer a money-back guarantee?” 04.01.2025

In today's episode, we help a photographer decide whether to offer a money-back guarantee for his services. Learn how to build trust with clients while protecting your business from potential downsides. 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...

Ep. 2925 - Q&A: “How can I stand out in the coaching industry?” 03.01.2025

In today's episode, we help a leadership coach stand out in an oversaturated market. Learn how to identify your unique value, niche down, and attract your ideal clients with strategies that work. 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 listene...

Ep. 2924 - TBT: Cookie ATM Becomes Pop-Up Hit 02.01.2025

In this week's Throwback Thursday segment, we revisit two late-night bakers who created Oakland's first cookie ATM. They share how this bold experiment evolved into a thriving pop-up and DIY cookie kit 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 les...

Ep. 2923 - Side Hustle School Season 9 Starts TODAY 01.01.2025

We're back with an all-new season! Here's how year nine (!) of Side Hustle School will work. Introducing new features, music, and another 365 days of episodes.  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 we...

#2922 - Q&A: “How can I start an ‘adopt don’t shop’ pet business?” 31.12.2024

In today’s New Year’s Eve episode, we help a listener explore how to turn their passion for the ‘adopt, don’t shop’ movement into a profitable 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 note...

#2921 - First $1,000: Office Furniture Blog Stands Up for Profits 30.12.2024

In this week’s First $1,000 segment, we meet a web developer who turned his interest in ergonomic office furniture into a profitable side hustle. We explore how he built multiple niche websites that generated tens of thousands in commissions through Google AdSense. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting t...

#2920 - Q&A: “Why did you give away your ‘Doing Things’ course?” 29.12.2024

In today’s episode, we dive into the strategy behind giving away an online course for free. Was this a crazy idea, a strategic plan, or something else? 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...

#2919 - Q&A: “What are your predictions for next year?” 28.12.2024

In today’s episode, we dive into predictions for 2025—which is right around the corner! What trends, opportunities, and challenges should side hustlers and small business owners be preparing for? 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 listene...

#2918 - Failure Friday: The Multi-Platform Freelance Overload 27.12.2024

In this week's “Failure Friday” segment, we hear from a freelance graphic designer who found success on Upwork and decided to expand to Fiverr to grow her client base. However, the move to Fiverr led to a decline in client quality, causing issues with project expectations and delivery. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ea...

#2917 - TBT: Analyst Turns Card Comparison Into Cash 26.12.2024

In this week's “Throwback Thursday” segment, we hear from a fin-tech employee whose side project comparing credit cards grew into a profitable venture, earning $8,000/month in referral fees. 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...

#2916 - Q&A: “What are the top 3 things I should do next?” 25.12.2024

Merry Christmas! In today's episode, we help a listener decide what to focus on next after gaining early traction with their side hustle. 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: SideHustleSc...

#2915 - Q&A: “Best tools for managing a shared business inbox?” 24.12.2024

In today's episode, we help a listener find the best way to co-manage a business email account with their team, including HelpScout, Hubspot, and more. 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...

#2914 - First $1,000: Data Analyst Codes Fantasy Sports Teams 23.12.2024

In this story, we follow a data analyst who turns his knack for numbers and love of sports into a profitable business. We explore how he developed fantasy sports prediction algorithms that helped him reach his first $1,000 in earnings. 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...

#2913 - Q&A: “How do I understand ROI when buying a local business?” 22.12.2024

In today's episode, we help a listener understand how to calculate ROI when considering buying a local business. We'll cover how to estimate the payoff period, factors that impact profitability, and tools to make the analysis easier. 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 in...

#2912 - Q&A: “I’ve been paying for subscriptions I don’t use!” 21.12.2024

In today's episode, we help a listener figure out what to do after paying for multiple subscriptions they haven't used: a common and unfortunate problem. 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 not...

#2911 - Failure Friday: When My Side Hustle Took Over My Life 20.12.2024

In this week's “Failure Friday” segment, we hear from a tech professional who started offering design and development services as a side hustle. As the business grew, balancing it with a full-time job and personal life becomes overwhelming, leading to stress and performance issues at work. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people wh...

#2910 - TBT: Graphic Artist Taps Into Planner Craze 19.12.2024

In this week's “Throwback Thursday” segment, we hear from a side hustler whose passion for organization and design morphed into a steady income stream while maintaining her day job. 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...

#2909 - Q&A: “How can I increase the average price per order for my online store?” 18.12.2024

In today's episode, we help a listener with strategies to boost the average order value of her online store. We'll cover upselling, cross-selling, and other techniques to increase sales in a way that feels natural and customer-friendly. 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...

#2908 - Q&A: “Should I hire micro-influencers to promote my brand?” 17.12.2024

In today's episode, we help a listener decide whether to use micro-influencers to promote their e-commerce brand. Should they hire through an agency or go the DIY route to save money? 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 se...

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