Side Hustle School

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Episodes

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Side Hustle School

Chris Guillebeau / Onward Project•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.

Sales and Distribution by Lemonada Media https://lemonadamedia.com/

Episodes

#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, 2023•5 min•Ep 2274•Transcript available on Metacast

#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, 2023•6 min•Ep 2273•Transcript available on Metacast

#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, 2023•4 min•Ep 2272•Transcript available on Metacast

#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, 2023•4 min•Ep 2271•Transcript available on Metacast

#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, 2023•4 min•Ep 2270•Transcript available on Metacast

#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, 2023•4 min•Ep 2269•Transcript available on Metacast

#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, 2023•5 min•Ep 2268•Transcript available on Metacast

#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, 2023•5 min•Ep 2267•Transcript available on Metacast

#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, 2023•5 min•Ep 2266•Transcript available on Metacast

#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, 2023•4 min•Ep 2265•Transcript available on Metacast

#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, 2023•4 min•Ep 2264•Transcript available on Metacast

#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, 2023•5 min•Ep 2263•Transcript available on Metacast

#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, 2023•4 min•Ep 2262•Transcript available on Metacast

#2261 - Q&A: “How do I choose a legal structure for my side hustle?”

A new web developer wants to make sure they set up their business in a way that is efficient and effective, but they're not sure where to start. Let's see if we can help them find a solution. 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...

Mar 11, 2023•4 min•Ep 2261•Transcript available on Metacast

#2260 - Failure Friday: The Influencer Who Quit Instagram

In this week’s Failure Friday segment, we hear from an aspiring influencer on her unsuccessful attempt to become a professional Instagrammer … which ended with her quitting the platform altogether. 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.co...

Mar 10, 2023•7 min•Ep 2260•Transcript available on Metacast

#2259 - TBT: “Car Parts Guy” Becomes Professional Reseller

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Chicago car parts reseller. After his first couple of years scouring junkyards for deals, he now sources most of his goods online. 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@side...

Mar 09, 2023•5 min•Ep 2259•Transcript available on Metacast

#2258 - Q&A: “Should I go into business with my best friend?”

This caller’s best friend is gung-ho on starting a business with her, but the caller has concerns. How can she determine if this is the right decision for both of them? 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: SideHustleS...

Mar 08, 2023•5 min•Ep 2258•Transcript available on Metacast

#2257 - Q&A: “An EV car rental side hustle??”

Sarah from Los Angeles is on the line today, and she's got a big idea brewing. Specifically, she’s thinking about starting a car rental business, but with a twist. Is there room in the market for a small, sustainable rental car brand? 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...

Mar 07, 2023•5 min•Ep 2257•Transcript available on Metacast

#2256 - First $1,000: Spotify Musician Gets Paid for Yoga Streams

In this week’s First $1,000 segment, we hear from an independent musician who earns passive income from Spotify, focusing on keywords and playlists related to yoga. 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 06, 2023•5 min•Ep 2256•Transcript available on Metacast

#2255 - Q&A: “A home-based meal delivery service for New York…”

Today’s caller has set his sights on starting a home-based meal delivery service, but wants to make sure he's covering all his bases. Let’s get him on the road to many five-star reviews! 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...

Mar 05, 2023•5 min•Ep 2255•Transcript available on Metacast

#2254 - Q&A: “I’m starting an Edible Insect Farm…”

You read that right. This idea might seem buggy, but there could be a real market for it. 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 Connect on Twitter: @chrisguillebeau Connect on Instagram: ...

Mar 04, 2023•5 min•Ep 2254•Transcript available on Metacast

#2253 - Failure Friday: ‘Helicopter Parent’ Disrupts Online Tutoring Session

In this week’s Failure Friday segment, we hear from a self-described “former online tutor.” His business started well, but was soon challenged by a difficult parent. 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: SideHustleScho...

Mar 03, 2023•5 min•Ep 2253•Transcript available on Metacast

#2252 - TBT: Children’s Party Hostess Makes Magic and Money

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Little Princess Parties, a children’s party hosting 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 Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/qu...

Mar 02, 2023•4 min•Ep 2252•Transcript available on Metacast

#2251 - Q&A: “Mobile photo booths for events and parties…”

Today’s caller is interested in starting a mobile photo booth business, but wants to make sure she has a solid plan in place. Let's help Janet turn her dream into a thriving 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 Email: team@sidehustleschool.com Be on the sh...

Mar 01, 2023•5 min•Ep 2251•Transcript available on Metacast

#2250 - Q&A: “Can you pay taxes on a credit card to earn cash back?”

Tax season is coming up for many of us in the U.S., so today a caller wants to know about paying taxes on a credit card that offers cash back. Is this an all-new 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: Side...

Feb 28, 2023•5 min•Ep 2250•Transcript available on Metacast

#2249 - First $1,000: Bali Nomad Writes Copy for Local Businesses

\ In this week’s First $1,000 segment, we hear from an Australian expat who moves to Bali to become a digital nomad. This is the story of his first $1,000 as a freelance copywriter. 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...

Feb 27, 2023•4 min•Ep 2249•Transcript available on Metacast

#2248 - Q&A: “Managing inventory for digital items…”

If you’re selling a digital product, isn’t your inventory unlimited? This might sound like a trick question, but there’s more to it. When you continue to add more and more digital products to their online store, there might be a downside. 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: SideHustleS...

Feb 26, 2023•5 min•Ep 2248•Transcript available on Metacast

#2247 - Q&A: “How to become a Medical Billing Advocate?”

A caller is wondering about becoming a Medical Billing Advocate. This is someone who helps patients negotiate and lower their medical bills, especially in cases where the bill is high and might include mistakes or unnecessary charges. 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...

Feb 25, 2023•5 min•Ep 2247•Transcript available on Metacast

#2246 - Failure Friday: “My business was like a coupon, it expired too soon…”

In this week’s Failure Friday segment, we hear from someone who started a coupon directory website. Unfortunately, he ended up spending more money than he saved. 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...

Feb 24, 2023•7 min•Ep 2246•Transcript available on Metacast

#2245 - TBT: “I've been keeping bees for the past five years…”

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Bay Area beekeeper who slings honey to the tune of $40,000/year 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: SideHustleSchool.com/qu...

Feb 23, 2023•5 min•Ep 2245•Transcript available on Metacast