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

#2356 - Q&A: “How should I handle freelance contracts?”

A freelance writer is using Chat-GPT to help draft his articles. So far, so good—but he needs help with figuring out client contracts. 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 Twi...

Jun 14, 20235 minEp. 2356

#2355 - Q&A: “I'm a seamstress with an interest in historical fashion…”

A Chicago seamstress with a passion for historical fashion wants to create and rent out period costumes. How can we help her go back in 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: [email protected] Be on the show: SideHustleSchool.com/questions Connect...

Jun 13, 20235 minEp. 2355

#2354 - First $1,000: Personal Paparazzo Welcomes Los Angeles Visitors

In this week’s First $1,000 segment, we hear from a “personal paparazzo” who does photo shoots for locals and visitors to the greater Los Angeles area. 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/questio...

Jun 12, 20235 minEp. 2354

#2353 - Q&A: “Social ads for event planning…”

A Boston side hustler is considering using social media ads as her marketing strategy. But like many first-time advertisers, she's unsure about how much to spend, where to start, and how to design her ads for maximum impact. 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...

Jun 11, 20235 minEp. 2353

#2352 - Q&A: “Promoting affiliate brands on my travel blog…”

A travel enthusiast who’s been documenting her adventures on a blog is ready to monetize her platform. How can she do so authentically? 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 Tw...

Jun 10, 20235 minEp. 2352

#2351 - Failure Friday: Fortune Cookie Writer Fails to Foresee Profit

In this week’s Failure Friday segment, we hear about a potential business of writing fortunes for fortune cookies. Sadly, this isn’t the story of the next Tesla or Amazon. 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...

Jun 09, 20236 minEp. 2351

#2350 - TBT: Biotech Recruiter Earns Commission for Job Placements

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an Indian-born woman who moves to the U.S. and starts a side hustle as a recruiter for biotech employees. After finishing grad school and building the business, she now does it 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 ...

Jun 08, 20236 minEp. 2350

#2349 - Q&A: “How does a dog trainer start selling dog toys?”

Being a dog trainer is so 2020. The real money is in dog toys! Let’s see if we can help this listener go from “woof” to “wow.” 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: @c...

Jun 07, 20235 minEp. 2349

#2348 - Q&A: “I feel overwhelmed by Shopify…”

A listener in Ottawa has recently opened a Shopify store, and finds the popular platform to be overwhelming. Can we simplify the process? 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 ...

Jun 06, 20235 minEp. 2348

#2347 - First $1,000: Florida Woman Becomes Pet Party Planner

In this week’s First $1,000 segment, we hear from the go-to pet party planner of St. Petersburg, Florida. She plans doggie bashes and cat-a-versary parties. 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...

Jun 05, 20235 minEp. 2347

#2346 - Q&A: “I have so many exciting ideas!”

Today we've got Sam on the line from Massachusetts. He’s wrestling with a conundrum many of our listeners may find familiar: several exciting ideas for a side hustle, but trouble in deciding which one to pursue. 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@sideh...

Jun 04, 20235 minEp. 2346

#2345 - Q&A: “Navigating regulations for selling herbal remedies…”

A Utah botanist wants to sell teas and tinctures, but also wants to make sure she follows local regulations. Let’s put our green thumbs to work and see if we can help. 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...

Jun 03, 20234 minEp. 2345

#2344 - Failure Friday: “Fake Wedding Guest” Biz Fizzles Out

In this week’s Failure Friday segment, we hear from a side hustler who tries selling a service as a fake wedding guest who helps to fill seats for brides and grooms while getting the party started on the dance floor. 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@...

Jun 02, 20236 minEp. 2344

#2343 - TBT: Vancouver Bike Tours Takes Scenic Route

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of a cycling tour business that serves visitors and locals. 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...

Jun 01, 20235 minEp. 2343

#2342 - Q&A: “How can I host a yoga and wellness retreat?”

Today’s caller is a yoga instructor with a vision to organize wellness retreats in serene locations. Let’s stretch our minds and see if we can help. 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 ...

May 31, 20234 minEp. 2342

#2341 - Q&A: “There’s no money in personal training…”

Most personal trainers that I’ve talked to agree on one thing: there’s not much money in just the personal training. This is true even when it’s expensive! Today’s caller wants to transition from in-person, individual sessions to online group classes. What’s the best strategy here? 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 sev...

May 30, 20235 minEp. 2341

#2340 - 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 29, 20236 minEp. 2340

#2339 - Q&A: “How to offer content strategy services…?”

As a successful freelance copywriter, today’s caller is looking to transition into content strategy. How can he rebrand himself and find clients in this new space? 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...

May 28, 20235 minEp. 2339

#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 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@sideh...

May 27, 20235 minEp. 2338

#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 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 sho...

May 26, 20236 minEp. 2337

#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 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...

May 25, 20236 minEp. 2336

#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 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 ...

May 24, 20236 minEp. 2335

#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