Side Hustle School - podcast cover

Side Hustle School

Chris Guillebeau sidehustleschool.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.

Hosted on Acast. See acast.com/privacy for more information.

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Episodes

#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: team@sidehustleschool.com 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: team@sidehustleschool.com 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: team@sidehustleschool.com 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: team@sidehustleschool.com 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: team@sidehustleschool.com 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: team@sidehustleschool.com 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: team@sidehustleschool.com 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: team@sidehustleschool.com 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: team@sidehustleschool.com Be on the show: SideHustleSchool.c...

Mar 25, 20235 minEp. 2275

#2274 - Failure Friday: “My first client was a total nightmare…”

In this week’s Failure Friday segment, we hear from a woman who had a goal of becoming a personal shopper, but was stymied by a difficult client. 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.com Be on the show: SideHustleSchool.com/questions Con...

Mar 24, 20235 minEp. 2274

#2273 - TBT: Destination Wedding Officiant Travels Worldwide

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a destination wedding officiant who helps couples say their vows in faraway locales. 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.com Be on the show: SideHustleSchoo...

Mar 23, 20236 minEp. 2273

#2272 - Q&A: “How can customer feedback improve my marketing?”

Gathering feedback from customers is an important tool for any small business owner, but it can be challenging to know how to use it effectively. Today, a caller seeks advice on how to incorporate feedback into a marketing plan. 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 ...

Mar 22, 20234 minEp. 2272

#2271 - Q&A: “How can I become a sustainability consultant?”

With a background in environmental science and a passion for sustainability, today’s caller from Seattle is ready to launch a Sustainability Consultancy. But how can she reach her target audience and make her business a 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 ...

Mar 21, 20234 minEp. 2271

#2270 - First $1,000: Health & Wellness Writer Establishes Side Income

In this week’s First $1,000 segment, we hear from a freelance writer who works in the health and wellness field. She now earns several thousand dollars a 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 each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustl...

Mar 20, 20234 minEp. 2270

#2269 - Q&A: “What are the most effective ways to promote my side hustle?”

Sarah has a unique skill set—she’s a reiki practitioner—and is eager to put it to work in a side hustle. But how do you get the word out there in today's digital age? 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.com Be on the show: SideHustleSch...

Mar 19, 20234 minEp. 2269

#2268 - Q&A: “How do I handle the transition from side hustle to full-time business?”

Today’s caller is ready to go from side hustle to full-time business! It’s always exciting when this happens, but it also produces questions and concerns. 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.com Be on the show: SideHustleSchool.com/ques...

Mar 18, 20235 minEp. 2268

#2267 - Failure Friday: The “American Ninja Warrior” Personal Trainer

In this week’s Failure Friday segment, we hear from a personal trainer who wanted to specialize to succeed in a crowded field. The problem was, the specialization he chose may have been too specialized, or perhaps too intimidating. 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...

Mar 17, 20235 minEp. 2267

#2266 - TBT: Successful Screenwriter Becomes Screenplay Consultant

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a freelance screenplay editor in Hollywood. In his new sideline, he consults on scripts from other aspiring screenplay wordsmiths. 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 16, 20235 minEp. 2266

#2265 - Q&A: “Planning for a Haunted House in Dallas…”

Today's caller has a spooky idea. She wants to create a haunted house attraction, but she needs some guidance in bringing it to life. Don’t be scared! Let’s help her 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustl...

Mar 15, 20234 minEp. 2265

#2264 - Q&A: “Indoor Vertical Farming has a lot of potential…”

Today we’ll hear from a listener who’s passionate about sustainable agriculture and believes that indoor vertical farming is the way of the future, especially for those living in big cities. How can she turn this into a 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 notes: SideHustleSchool.com...

Mar 14, 20234 minEp. 2264

#2263 - First $1,000: Michigan Accountant Moonlights as Engagement Photographer

In this week’s First $1,000 segment, we hear from Elaine in Wayne County, Michigan. She’s an accountant for her day job and works as an engagement photographer for her side hustle. 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.com Be on the show:...

Mar 13, 20235 minEp. 2263

#2262 - Q&A: “My dream is to own a Mobile Adventure Park…”

Today's caller is taking a leap of faith with a new and unique idea for a mobile adventure park. How can she make her vision a reality on a low budget? 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.com Be on the show: SideHustleSchool.com/questio...

Mar 12, 20234 minEp. 2262
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