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

#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 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@...

May 23, 20234 minEp. 2334

#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 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...

May 22, 20236 minEp. 2333

#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 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/quest...

May 21, 20234 minEp. 2332

#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 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/ques...

May 20, 20235 minEp. 2331

#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 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...

May 19, 20236 minEp. 2330

#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 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...

May 18, 20235 minEp. 2329

#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 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...

May 17, 20235 minEp. 2328

#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, 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: ...

May 16, 20235 minEp. 2327

#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 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...

May 15, 20235 minEp. 2326

#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 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: Si...

May 14, 20235 minEp. 2325

#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 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 Conn...

May 13, 20235 minEp. 2324

#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, 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: ...

May 12, 20236 minEp. 2323

#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 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...

May 11, 20236 minEp. 2322

#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 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 Twit...

May 10, 20236 minEp. 2321

#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 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@sidehustlesch...

May 09, 20235 minEp. 2320

#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 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...

May 08, 20236 minEp. 2319

#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 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/...

May 07, 20235 minEp. 2318

#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 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...

May 06, 20234 minEp. 2317

#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 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...

May 05, 20237 minEp. 2316

#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 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@sidehustlesch...

May 04, 20236 minEp. 2315

#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 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 Connec...

May 03, 20235 minEp. 2314

#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 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...

May 02, 20234 minEp. 2313

#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 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/question...

May 01, 20238 minEp. 2312

#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 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 ...

Apr 30, 20235 minEp. 2311

#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 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: @chrisguillebeau Conn...

Apr 29, 20235 minEp. 2310

#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 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 Twitte...

Apr 28, 20237 minEp. 2309

#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 than $4,000/month part-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 e...

Apr 27, 20237 minEp. 2308

#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 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 E...

Apr 26, 20236 minEp. 2307

#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 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: @chrisgui...

Apr 25, 20235 minEp. 2306

#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 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/question...

Apr 24, 20236 minEp. 2305