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

#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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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

#2866 - Q&A: "How can I use A/B testing to improve my website conversion rate?"

In this episode, we explore how to use A/B testing to boost your website conversion rate. Sometimes the simplest changes make a huge improvement! 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: [email protected] Be on the show: SideHustleSchool.com/questions Con...

Nov 05, 20246 minEp. 2866

#2865 - First $1,000: From Spreadsheets to Secret Shopping

In this week’s “First $1K” segment, we hear from an accountant who turned her attention to detail and data collection skills into a side gig as a mystery shopping evaluator. 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: [email protected] Be on the show: SideHu...

Nov 04, 20246 minEp. 2865

#2864 - Q&A: “How to assess market demand for your side hustle?”

In this episode, we discuss how to assess the market demand for your side hustle idea. Can you know in advance if your idea will succeed? 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: [email protected] Be on the show: SideHustleSchool.com/questions Connect on ...

Nov 03, 20245 minEp. 2864

#2863 - Q&A: “What are some good business ideas for teens?”

In this episode, we explore business ideas for teens and pre-teens, from pet sitting to digital services. Learn how to guide your kids in starting and managing their own ventures without overwhelming them. 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 02, 20245 minEp. 2863

#2862 - Failure Friday: Stock Photo Platform Lowers Commissions

In this week’s Failure Friday segment, we meet a landscape photographer whose thriving side hustle on Shutterstock comes crashing down after a sudden policy change: a classic case of “don’t put all your stock photos in one basket.” 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...

Nov 01, 20246 minEp. 2862

#2861 - TBT: An Architect’s Side Hustle in 3D Real Estate Modeling

In this week’s “Throwback Thursday” segment, we hear from an architect who turned his skills in 3D modeling and rendering into a successful side hustle, helping real estate agents bring their listings to life. 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@sidehus...

Oct 31, 20245 minEp. 2861

#2860 - Q&A: “Launching a silent disco service!”

In this episode, we discuss how to start a silent disco service for events and corporate clients. What are the essential equipment requirements, logistics, and ways to find your first clients? 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: [email protected] Be ...

Oct 30, 20246 minEp. 2860