Side Hustle School

By Chris Guillebeau / Onward Project

Business Careers

What's Side Hustle School about?

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.

4.7

3,001 ratings

Download our free app to listen on your phone

LAST EPISODE

#2338 - Q&A: “Selling tote ...

05.27.2023

Does the world need more tote bags? Apparently the answer is… maybe! Let’s hear from a listener selling eco-friendly tote bags at local markets and online. They’re wondering about the right time to raise prices. Side Hustle School features a ...

Side Hustle School episodes:

05.27.2023 #2338 - Q&A: “Selling tote bags, but need to raise prices…” Does the world need more tote bags? Apparently the answer is… maybe! Let’s hear from a listener selling eco-friendly tote bags at local markets and online. They’re wondering about the right time to raise prices. Side Hustle School features a ...
05.26.2023 #2337 - Failure Friday: Rent-a-Friend Fails to Launch in Tulsa In this week’s Failure Friday segment, we hear from a small-town side hustler who tries to follow a popular business model from Japan. Unfortunately, the idea is lost in translation. Side Hustle School features a new episode EVERY DAY, featuring ...
05.25.2023 #2336 - TBT: Social Media Manager Earns $4,000/Month Part-Time In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a social media manager who focuses on female fitness coaches and influencers. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
05.24.2023 #2335 - Q&A: “I sell pet bandanas. How can I reach pet influencers on Instagram?” She sells handmade pet bandanas, and wants to take her business to the next level—but she’s struggling with pet influencers not getting back to her. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...
05.23.2023 #2334 - Q&A: “Going from weddings to corporate photography…” A semi-professional photographer has been specializing in wedding photography, and is now looking to expand his services into corporate events and product photography. How can he do this while maintaining his income? Side Hustle School features a new episode EVERY ...
05.22.2023 #2333 - First $1,000: Home Improvement Employee Moonlights as Renovation Aide In this week’s First $1,000 segment, we hear from someone who works at a home improvement store by day—and moonlights by advising homeowners on renovation projects. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
05.21.2023 #2332 - Q&A: “I’m adding a subscription box for soaps…” A listener who sells handmade soap is considering adding a subscription box service, where customers receive a curated selection of products every month. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ...
05.20.2023 #2331 - Q&A: “Cost-effective marketing strategies?” Today's caller is on a mission to find cost-effective marketing strategies for their side hustle. How do you get the word out without spending much money? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
05.19.2023 #2330 - Failure Friday: Chicken Rental Service Fails to Egg-cite In this week’s Failure Friday segment, we hear from a Boise entrepreneur with the goal of bringing chickens to city dwellers. Alas, in the end the business is forced to flee the coop. Side Hustle School features a new episode ...
05.18.2023 #2329 - TBT: Handywoman Offers DIY Home Repair Workshops In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Washington handywoman who operates a series of DIY Home Repair workshops. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
05.17.2023 #2328 - Q&A: “Voiceover artist offers voiceover coaching…” A voiceover question from a voiceover artist on potential voiceover coaching for voiceover clients. Did you get that? Hint: it’s about voiceover. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra ...
05.16.2023 #2327 - Q&A: “Reaching the right audience with digital prints…” In today's episode, we have a question from a listener working on a side hustle creating and selling digital art prints online. How can he discover and reach the perfect audience? Side Hustle School features a new episode EVERY DAY, ...
05.15.2023 #2326 - First $1,000: Baltimore Photographer Starts Drone Instruction In this week’s First $1,000 segment, we hear from a Baltimore photographer who finds inspiration high in the sky. His new business teaching drone photography is taking off! Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
05.14.2023 #2325 - Q&A: “I'm looking to leverage my existing skills…” In today’s episode, a talented graphic designer and marketer searches for a fulfilling side hustle that capitalizes on her existing skill set. How can you find one for yourself? Side Hustle School features a new episode EVERY DAY, featuring detailed ...
05.13.2023 #2324 - Q&A: “I want to offer home staging services…” A listener in Vancouver wants to start a home staging side hustle. How can she build a portfolio of clients and develop the right relationships? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...
05.12.2023 #2323 - Failure Friday: “Looking back on my picnic misadventures…” In this week’s Failure Friday segment, we hear from a Miami caterer who had a cute idea to sell customized picnic lunches. Unfortunately, things didn’t turn out the way she hoped. Side Hustle School features a new episode EVERY DAY, ...
05.11.2023 #2322 - TBT: Mobile Pet Grooming Thrives in Oakland In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a startup employee offering a mobile pet grooming side hustle in Oakland, California. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
05.10.2023 #2321 - Q&A: “I’m a language tutor… and I need more students!” A language tutor in Boston wants to focus more on her sessions and less on bringing in new students. How can she become fully booked? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...
05.09.2023 #2320 - Q&A: “Handmade pottery sales have plateaued…” A listener in Minnesota has been running a side hustle selling handmade pottery on Etsy for about a year. He had a good start with sales but has since plateaued—how can we get him back on the fast track? Side ...
05.08.2023 #2319 - First $1,000: “I wanted to explore AI-generated art…” In this week’s First $1,000 segment, we hear from a real estate professional who makes and sells design elements that come from AI-generated art. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ...
05.07.2023 #2318 - Q&A: “How can I make eco-friendly surfboard wax??” We've got a gnarly question today from Brad in San Diego: how can this software developer and surfer start a side business selling eco-friendly surfboard wax? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
05.06.2023 #2317 - Q&A: “Building a network as an introvert…” Building a strong network is vital for side hustle success, but today’s caller is an introvert. Should he just “get over it,” or are there strategies he can use to succeed on his own terms? (Hint: door number two.) Side ...
05.05.2023 #2316 - Failure Friday: “Puzzlemaster of Cleveland” Fails to Break Even In this week’s Failure Friday segment, we hear from a city engineer who tries to bring “game night” to companies. Alas—it doesn’t turn into a puzzling success. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
05.04.2023 #2315 - TBT: Tiny Home Consultant Designs Bespoke Blueprints In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a location independent editor who has a sideline as a tiny home consultant. Like its industry, this side hustle is growing! Side Hustle School features a ...
05.03.2023 #2314 - Q&A: “I’m a personal chef in New York City…” An NYC personal chef wants to offer personalized cooking classes focused on healthy, plant-based meals. How can she attract the right clients? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra ...
05.02.2023 #2313 - Q&A: “Structuring a freelance writing program…” In this lively episode, we'll hear from a seasoned freelance writer with a background in journalism. He wants to make a coaching program—but how will he compete with AI? Side Hustle School features a new episode EVERY DAY, featuring detailed ...
05.01.2023 #2312 - First $1,000: “BritBox” Sends British-Themed Goods Worldwide In this week’s First $1,000 segment, we hear from the founder of BritBox, a service that sends British-themed goods to lonely expats around the world. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...
04.30.2023 #2311 - Q&A: “Struggling to balance day job, family, and online boutique…” If you're feeling overwhelmed by multiple commitments, this episode will give you three practical tips to help you streamline your side hustle without compromising your main priorities. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
04.29.2023 #2310 - Q&A: “How can I start a personal shopping business?” A caller is interested in starting a personal shopping business. What’s the best way to approach this idea? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their ...
04.28.2023 #2309 - Failure Friday: “Ultimate Wrinkle Inducer” MLM Flops In this week’s Failure Friday segment, we hear from an office manager who gets sucked into a makeup MLM and lives to tell the tale. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...
04.27.2023 #2308 - TBT: “I transformed from work-from-home coach to corporate consultant…” In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a work-from-home coach who started her side hustle at the beginning of the pandemic. After pivoting to focus on companies training their employees, she earns more ...
04.26.2023 #2307 - Q&A: “I want to do audio production for podcasts…” Today we hear from Michael in Delaware, who’s interested in starting a podcast production business as a side hustle. He’s got the experience with audio production, but isn’t sure where to begin with the business side of things. Side Hustle ...
04.25.2023 #2306 - Q&A: “I’m building a grocery-shopping app…” A listener is developing a mobile app to “revolutionize the way people shop for groceries.” How can they get it funded? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money ...
04.24.2023 #2305 - First $1,000: Indian Woman Helps Indian Men Improve Dating Profiles In this week’s First $1,000 segment, we hear from Priya in Bangalore. She has a side hustle helping men with their dating profiles—and she keeps busy! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
04.23.2023 #2304 - Q&A: “Sell more from my organic farm…” A listener is struggling to find new customers for her organic farm produce. Should she drop out of farmers’ school, or put her hand to the plow? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
04.22.2023 #2303 - Q&A: “I’m an accountant—how do I specialize?? As a solopreneur, this Canadian account is concerned that “choosing a niche” could mean losing his existing clients who don't meet that speciality. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ...
04.21.2023 #2302 - Failure Friday: Airbnb Is Harder Than It Looks In this week’s Failure Friday segment, we hear from a New York City resident who tries—and fails—to navigate the city’s tough rules on rentals. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ...
04.20.2023 #2301 - TBT: Camera Affiliate Earns $100,000 in Commissions In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a camera gear affiliate who earns thousands of dollars a month from commissions. He’s earned more than $100k so far! Side Hustle School features a new ...
04.19.2023 #2300 - Q&A: “When’s the right time to scale up?” A listener is in the exciting but uncertain phase of considering whether to transition his growing freelance web design side hustle into a full-time business. How can he make the wisest decision? Side Hustle School features a new episode EVERY ...
04.18.2023 #2299 - Q&A: “3D-printed prosthetics for marine animals…” Here’s a new one: this caller wants to create customized 3D-printed prosthetics for marine animals like sea turtles and dolphins. Crazy or brilliant? Let’s investigate! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...
04.17.2023 #2298 - First $1,000: City Government Staffer Leads Virtual Events In this week’s First $1,000 segment, we hear from a virtual events planner. If you need a virtual wedding, networking event, or gender reveal party, she’s got it covered! Side Hustle School features a new episode EVERY DAY, featuring detailed ...
04.16.2023 #2297 - Q&A: “How can I market my online yoga course?” In this episode, a yoga instructor looks to expand her business beyond the confines of her local studio. But how can she compete with so much free content? Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
04.15.2023 #2296 - Q&A: “Looking for low-risk, high-reward side hustles…” Our listener, Brenda, is a single mom with a full-time job, looking to supplement her income from the comfort of her home. Accordingly, we’ll be diving into the world of low-risk, high-reward side hustles! Side Hustle School features a new ...
04.14.2023 #2295 - Failure Friday: Flip Phone Reselling Fails to Cell Phones In this week’s Failure Friday segment, we hear from a serial side hustler with the brilliant idea to sell flip phones—because who doesn’t want a flip phone, amiright? In the end, he couldn’t “cell” a single phone. Side Hustle School ...
04.13.2023 #2294 - TBT: eBay Consignment Seller Never Runs Out of Inventory In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an eBay consignment seller who decided to focus on selling items for other people for a commission. How much commission? How does it work? Let’s find ...
04.12.2023 #2293 - Q&A: “It’s hard to separate work from personal life…” In this episode, we're addressing a concern that many freelancers, remote workers, and side hustlers can relate to: striking the right work-life balance and staying motivated. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
04.11.2023 #2292 - Q&A: “Makin’ a dog walkin’ app…” Woof! Today’s caller is a longtime listener with an idea for a mobile app that connects dog owners with local dog walkers. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra ...
04.10.2023 #2291 - First $1,000: Sign Language Interpretation Pays for Europe Trip In this week’s First $1,000 segment, we hear from a school counselor with a side hustle in sign language interpretation. The extra income she earns goes to a college fund for her daughter, as well as a summer trip to ...
04.09.2023 #2290 - Q&A: “A social network to connect seniors with volunteers…” Our caller from Canada has an idea for a social network that connects senior citizens with volunteer "grandchildren" for companionship. How does it work, and will it be hard to compete with existing services like Facebook? Side Hustle School features ...
04.08.2023 #2289 - Q&A: “Bakin' cupcakes for fun and money…” Today’s caller likes cupcakes (who doesn’t??) and they want to turn their love of sweet treats into regular revenue. Live from the kitchen, let’s see what we can mix up! Side Hustle School features a new episode EVERY DAY, featuring ...

Older episodes