Side Hustle School - podcast cover

Side Hustle School

Chris Guillebeau / Onward Projectsidehustleschool.com

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/  

Episodes

Ep. 2934 - Weekend Workshop: Beg, Borrow, or Steal Ideas

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: the power of observation. 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...

Jan 12, 20257 minEp. 2934

Ep. 2933 - Q&A: “How do I know if my idea is going to work?”

In today’s episode, we help a listener validate their idea for a carpooling app for parents. Learn how to test demand, estimate costs, and spot red flags before investing too much time or 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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool...

Jan 11, 20256 minEp. 2933

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

    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 free guided lessons and listener Q&A several days each week. Show notes: SideHustleScho...

Jan 10, 20255 minEp. 2932

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

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 quitting their job. This year, the show includes free guided lessons and listener Q&A several ...

Jan 09, 20257 minEp. 2931

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

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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschoo...

Jan 08, 20256 minEp. 2930

Ep. 2929 - Q&A: “What can I learn from my website analytics?”

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 and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sid...

Jan 07, 20255 minEp. 2927

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

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, the show includes free guided lessons and listener Q&A several days each week. Sho...

Jan 06, 20256 minEp. 2928

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

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 year, the show includes free guided lessons and listener Q&A several days each week. ...

Jan 05, 202510 minEp. 2927

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

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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehust...

Jan 04, 20256 minEp. 2926

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

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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschoo...

Jan 03, 20256 minEp. 2925

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

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 lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email...

Jan 02, 20256 minEp. 2924

Ep. 2923 - Side Hustle School Season 9 Starts TODAY

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 week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: Si...

Jan 01, 20256 minEp. 2923

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

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 notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questi...

Dec 31, 20245 minEp. 2922

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

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 their job. This year, the show includes free guided lessons and listener Q&A several days each we...

Dec 30, 20246 minEp. 2921

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

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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questio...

Dec 29, 20246 minEp. 2920

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

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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com ...

Dec 28, 20245 minEp. 2919

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

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 earn extra money without quitting their job. This year, the show includes free guided lessons an...

Dec 27, 20247 minEp. 2918

#2917 - TBT: Analyst Turns Card Comparison Into Cash

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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehust...

Dec 26, 20246 minEp. 2917

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

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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Conne...

Dec 25, 20245 minEp. 2916

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

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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/q...

Dec 24, 20245 minEp. 2915

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

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 includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleScho...

Dec 23, 20246 minEp. 2914

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

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 includes free guided lessons and listener Q&A several days each week. Show notes: Side...

Dec 22, 20245 minEp. 2913

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

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 notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleScho...

Dec 21, 20245 minEp. 2912

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

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 who earn extra money without quitting their job. This year, the show includes free guided lesson...

Dec 20, 20247 minEp. 2911

#2910 - TBT: Graphic Artist Taps Into Planner Craze

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 Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool....

Dec 19, 20246 minEp. 2910

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

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 includes free guided lessons and listener Q&A several days each week. Show notes: S...

Dec 18, 20244 minEp. 2909

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

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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on ...

Dec 17, 20246 minEp. 2908

#2907 - First $1,000: Managing Airbnb Properties in Amsterdam

In this week’s “First $1K” segment, we hear from a Dutch side hustler who turned her organizational skills into a profitable business by managing Airbnb properties for homeowners. 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.com Email: team@sidehustleschool.co...

Dec 16, 20246 minEp. 2907

#2906 - Q&A: “I need a sales script for cold emailing potential clients!”

In today’s episode, we help a listener refine their cold email strategy to get more client responses. Learn how to craft personalized, value-driven messages that convert, without sounding like a template. 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.com Email: team@sidehu...

Dec 15, 20245 minEp. 2906

#2905 - Q&A: ““What’s the best ticketing strategy for my event?”

Today’s episode tackles a question about the best way to sell tickets for an event. Should you keep sales open on a rolling basis or create urgency with a waitlist and limited sale dates? 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.com Email: team@sidehustleschool.com Be...

Dec 14, 20245 minEp. 2905