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

#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 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...

Apr 23, 20234 minEp. 2304

#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 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 C...

Apr 22, 20234 minEp. 2303

#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 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 Conne...

Apr 21, 20237 minEp. 2302

#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 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]...

Apr 20, 20238 minEp. 2301

#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 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] ...

Apr 19, 20235 minEp. 2300

#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 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: SideHustleS...

Apr 18, 20235 minEp. 2299

#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 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: SideHustl...

Apr 17, 20236 minEp. 2298

#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 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/que...

Apr 16, 20235 minEp. 2297

#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 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...

Apr 15, 20237 minEp. 2296

#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 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...

Apr 14, 20235 minEp. 2295

#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 out! 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: SideHustleSchoo...

Apr 13, 20237 minEp. 2294

#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 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: Side...

Apr 12, 20235 minEp. 2293

#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 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 Twitter: @chris...

Apr 11, 20234 minEp. 2292

#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 Europe. 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 Emai...

Apr 10, 20236 minEp. 2291

#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 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:...

Apr 09, 20235 minEp. 2290

#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 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: SideHustle...

Apr 08, 20235 minEp. 2289

#2288 - Failure Friday: “I tried wearing lettuce on my head to get attention…”

In this week’s Failure Friday segment, we hear from an aspiring fashion blogger. After failing to catch the world’s attention with her belt-as-necklace feature, she tries wearing lettuce on her head. 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....

Apr 07, 20236 minEp. 2288

#2287 - TBT: Role-Playing Dungeon Master Earns $2,000/Month

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Canadian dungeon master who hosts tabletop role-playing games. This side biz brings in an extra $2,000/month. 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 o...

Apr 06, 20237 minEp. 2287

#2286 - Q&A: “Introducing the plant-based diet for pets…”

Today’s caller is interested in starting a plant-based pet food delivery service. With the growing demand for healthier and more sustainable options for pets, she’s identified what she sees as a unique opportunity. 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...

Apr 05, 20235 minEp. 2286

#2285 - Q&A: “An outdoor adventure and survival training school…”

Today we’ll hear from a caller with an idea for an outdoor adventure and survival training school for city-dwellers. You never know when this might come in handy… 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....

Apr 04, 20235 minEp. 2285

#2284 - First $1,000: “I watched home renovation shows and decided to try it…”

In this week’s First $1,000 segment, we hear from a listener who flips houses when he’s not at his job in middle management. He learned from watching TLC shows! 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.co...

Apr 03, 20235 minEp. 2284

#2283 - Q&A: “Staying motivated when life gets hectic…”

Life gets busy! How do you maintain motivation in the midst of it all? That’s what today’s listener is wondering about. I’ll give them—and you—three practical tips. 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: SideHustleSchoo...

Apr 02, 20234 minEp. 2283

#2282 - Q&A: “An AI-powered personal shopping service…”

Today's caller is looking to dive into the world of technology and fashion by starting an AI-powered personal shopping and styling service. She’s eager to get the ball rolling, but is also feeling overwhelmed by the prospect of starting a new 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...

Apr 01, 20236 minEp. 2282

#2281 - Failure Friday: Minimalism Expert Becomes Disillusioned

In this week’s Failure Friday segment, we hear from a woman who sets up to become a subject matter expert in the world of minimalism—before becoming uncomfortable with the commercial elements of the philosophy. 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...

Mar 31, 20236 minEp. 2281

#2280 - TBT: Corporate Exec Ditches Job for Side Hustle

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a freelance corporate auditor who leaves his corporate gig to strike out on his own, first as a side hustle and now full-time. 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@sidehustle...

Mar 30, 20235 minEp. 2280

#2279 - Q&A: “I’d like to offer Virtual Reality therapy…”

Today's caller is exploring the intersection of psychology and technology and wants to bring virtual reality (VR) to the world of therapy. Is this 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/q...

Mar 29, 20235 minEp. 2279

#2278 - Q&A: “Tips for handling customer service and support?”

You want to make sure you don’t end up in a situation where your limited side hustle time is spent only doing support—instead, you should be spending it on growing your business. But how do you do this, practically speaking? 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 Emai...

Mar 28, 20235 minEp. 2278

#2277 - First $1,000: Software Engineer Crafts Balloon Sculptures

In this week’s First $1,000 segment, we hear from an engineer who takes out his daytime frustrations on a series of side hustle balloon sculptures. He’s a self-described balloon-atic! 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 sh...

Mar 27, 20235 minEp. 2277

#2276 - Q&A: “I want to offer Creative Writing Workshops…”

Today’s caller has a passion for creative writing and wants to turn it into a side hustle by offering workshops. How can they go from idea to income? 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...

Mar 26, 20234 minEp. 2276

# 2275 - Q&A: “How can a designer stand out in a crowded market?”

The market for web design is getting more crowded every day, and today's caller is looking for advice on how to make her business stand out from the competition. 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.c...

Mar 25, 20235 minEp. 2275