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

#2896 - TBT: Home Gym Affiliate Earns $80,000

In this week’s “Throwback Thursday” segment, we hear from a side hustler whose passion for fitness transformed into a successful affiliate marketing blog. 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/ques...

Dec 05, 20246 minEp. 2896

#2895 - Q&A: “Should I record my videos in portrait or landscape mode?”

Today’s episode tackles a question about recording videos for multiple platforms. Should you shoot in portrait or landscape mode? And is there a way to record once and use the content everywhere? We’ve got answers and tips to streamline your video production. 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. Sh...

Dec 04, 20244 minEp. 2895

#2894 - Q&A: “Can I do Substack, TikTok, podcast, and a paid membership?”

In today’s episode, we help a creator who’s building a solo travel platform decide whether to focus on one content platform or expand to multiple channels like Substack, TikTok, and podcasts. 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 o...

Dec 03, 20245 minEp. 2894

#2893 - First $1,000: Building a Business One Signature at a Time

In this week’s First $1,000 segment, we hear from the owner of a California signature-gathering business, which collects signatures for ballot initiatives. He earns more than $1 on every signature—and this money adds up! 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: t...

Dec 02, 20247 minEp. 2893

#2892 - Q&A: “How will a new presidential administration impact side hustlers?”

Today’s episode addresses what a new presidential administration could mean for small business owners and side hustlers. We’ll cover possible tax changes, regulatory shifts, and access to funding. 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 01, 20245 minEp. 2892

#2891 - Q&A: “How to conduct competitor analysis for free?”

In today’s episode, we dive into free and effective ways to analyze your competition. Learn to use simple Google searches, free tools, and social media insights to keep your side hustle ahead of the game. 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@sidehustlesc...

Nov 30, 20245 minEp. 2891

#2890 - Failure Friday: Sugar-Coated Advice Crumbles Cake Dreams

In this week’s Failure Friday segment, we hear from a passionate baker whose custom cake business quickly rises, only to fall flat due to misguided pricing strategies and well-meaning but bad advice from loved ones. 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@s...

Nov 29, 20247 minEp. 2890

#2889 - TBT: From House Flipper to Rental Property Guru

In this week’s “Throwback Thursday” segment, we revisit a side hustler whose real estate investing experience evolved into helping families purchase their first rental properties in distressed cities. 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...

Nov 28, 20247 minEp. 2889

#2888 - Q&A: “How to create a simple customer loyalty program for a small business?”

On today’s episode, we’re talking about how to create a simple, low-maintenance customer loyalty program for your side business. Did someone say punch card? 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/qu...

Nov 27, 20245 minEp. 2888

#2887 - Q&A: “Is it easier or harder to start an online business today?”

In today’s episode, we explore whether it’s easier or harder to start an online business today compared to seven years ago. Find out how the landscape has changed and what it takes to stand out in a crowded market. 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@si...

Nov 26, 20245 minEp. 2887

#2886 - First $1,000: Licensing Digital Art to Cruise Lines

In this week’s “First $1K” segment, we hear from a digital artist who licensed their artwork to cruise lines for use on TVs and digital displays. Discover how this unique niche led to earning the artist 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. Show notes: SideHustleSchool.com Email: t...

Nov 25, 20246 minEp. 2886

#2885 - Q&A: “How to increase the perceived value of digital products?”

In today’s episode, we discuss how to package and present digital products in a way that increases their perceived value. 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 Connect on Instagram: @193c...

Nov 24, 20245 minEp. 2885

#2884 - Q&A: “Instagram Reels strategies for showcasing a product or service...”

On today’s episode, we’re breaking down how to use Instagram Reels to grow your side hustle. From product showcases to behind-the-scenes content, find out how you can create engaging Reels that capture attention and drive sales. 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 ...

Nov 23, 20245 minEp. 2884

#2883 - Failure Friday: Trademark Troubles Topple New Business

In this week’s Failure Friday segment, we follow a small business owner whose clever branding leads to an unexpected legal battle. 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 Connect on Instagr...

Nov 22, 20246 minEp. 2883

#2882 - TBT: The Unlikely Algae Entrepreneur

In this week’s “Throwback Thursday” segment, we catch up with the owner of a small-scale algae farm in Wisconsin who’s ridden the wave of plant-based supplement popularity. 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: SideHus...

Nov 21, 20246 minEp. 2882

#2881 - Q&A: “How to ask for and gather customer testimonials?”

In this episode, we explore the best ways to gather customer testimonials for your side hustle. This is important! 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 Connect on Instagram: @193countrie...

Nov 20, 20245 minEp. 2881

#2880 - Q&A: “How do you structure your day when balancing a 9-to-5 job?"

In this episode, we explore how to balance a full-time job with a side hustle. The struggle is real! 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 Connect on Instagram: @193countries Visit Chris'...

Nov 19, 20246 minEp. 2880

#2879 - First $1,000: Turning Personal Photos into Custom Jigsaw Puzzles

In this week’s “First $1K” segment, we hear from a side hustler who starts a custom jigsaw puzzle business, turning personal photos into unique puzzles sold on Etsy. 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...

Nov 18, 20247 minEp. 2879

#2878 - Q&A: "How to use LinkedIn to find freelance clients?”

In this episode, we dive into how to use LinkedIn to find your first freelance client. Discover simple strategies to optimize your profile, connect with the right people, and stand out in a crowded market. 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@sidehustles...

Nov 17, 20246 minEp. 2878

#2877 - Q&A: “How to use side hustle experience to negotiate a raise?”

In this episode, we discuss how to leverage your side hustlin’ experience to negotiate a raise or promotion at your 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.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @1...

Nov 16, 20245 minEp. 2877

#2876 - Failure Friday: Overworked Freelancer Gets Stressed Out

In this week’s Failure Friday segment, we meet a freelance writer whose eagerness to boost her side income leads to a scheduling nightmare. Organization is everything! 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: SideHustleSc...

Nov 15, 20247 minEp. 2876

#2875 - TBT: Paper Profits from Pop-Up Passion

In this week’s “Throwback Thursday” segment, we hear from the owner of a pop-up stationery business that’s evolved from occasional events to a thriving part-time enterprise. 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: SideHu...

Nov 14, 20246 minEp. 2875

#2874 - Q&A: “How can introverts sell and market effectively?”

In this episode, we explore strategies for introverts to market their side hustles without feeling overwhelmed. Such a thing is possible! 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 Connect on ...

Nov 13, 20245 minEp. 2874

#2873 - Q&A: “Tips for creating and monetizing ASMR content...”

In this episode, we explore how to start an ASMR content creation side hustle. (And if you don’t know what ASMR is, you’ll learn that too!) 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 Connect o...

Nov 12, 20246 minEp. 2873

#2872 - First $1,000: Nurse Earns Income Prepping for Disaster

In this week’s “First $1K” segment, we hear from a nurse who turned her expertise in health and safety into a side gig as a disaster preparedness consultant, helping individuals and businesses prep for emergencies. 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@si...

Nov 11, 20247 minEp. 2872

#2871 - Q&A: “How to use storytelling to market a side hustle?”

In this episode, we explore ways to use storytelling to market your side hustle or small business, and make it stand out with 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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on I...

Nov 10, 20245 minEp. 2871

#2870 - Q&A: “What does it take to make the New York Times bestseller list?”

In this episode, we reveal the magic number of copies you need to sell in one week to make the New York Times bestseller list. A caller from last month returns with an important follow-up! 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 t...

Nov 09, 20246 minEp. 2870

#2869 - Failure Friday: The Virtual Workout Fitness Flop

In this week’s Failure Friday segment, we follow a fitness coach's journey into the world of virtual workouts, where their DIY approach to social media marketing leads to disappointment. 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...

Nov 08, 20247 minEp. 2869

#2868 - TBT: Electrical Engineer Installs Smart Home Tech

In this week’s “Throwback Thursday” segment, we hear from an electrical engineer who turned his technical expertise into a thriving side gig installing smart home systems. 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: SideHust...

Nov 07, 20245 minEp. 2868

#2867 - Q&A: “Setting boundaries with clients … I need help!”

In this episode, we discuss strategies for setting boundaries with clients when your side hustle isn’t your main job. Learn how to communicate effectively, manage expectations, and maintain a healthy balance between your side hustle and full-time 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...

Nov 06, 20246 minEp. 2867