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

#1616 - Failure Friday: “The client ordered the most expensive thing on the menu…”

In this week’s Failure Friday segment, we hear from a “Reddit Secret Santa” who builds a whole business around an idea that started as a seasonal project. 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...

Jun 04, 20216 minEp. 1616

#1615 - TBT: Premium Cocktail Pins Offer “Negronis for Your Homies”

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-founder of a cocktail pin merchant. Bottoms 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: SideHustleSchool.com/questions Connect on ...

Jun 03, 20218 minEp. 1615

#1614 - Q&A: How do income-share agreements work?

A listener has learned about income-share agreements, where college tuition or other learning costs aren’t due until after graduation. Is this a good deal? 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/...

Jun 02, 20216 minEp. 1614

#1613 - Monogrammed Blanket Etsy Shop Measures Up

A simple embroidery shop becomes a six-figure blanket biz, podcast, and online course. 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 Connect on Instagram: ...

Jun 01, 20217 minEp. 1613

#1612 - Q&A: “Help! My lifestyle site is stuck at a plateau…”

A listener’s lifestyle site started well, but can’t seem to get past an early-stage plateau. What should she do? 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: @chrisguilleb...

May 31, 20216 minEp. 1612

#1611 - Intern Manages Businesses For Six-Figure Income

When a corporate intern searches for an off-ramp, she creates a new job title that leads to a full-time income and new online course. 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 T...

May 30, 20218 minEp. 1611

#1610 - Q&A: Will my web host design my website?

A listener wants to know if their web host offers a “full service” option, or if it’s better to find another way to get the job done. 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 T...

May 29, 20215 minEp. 1610

#1609 - Failure Friday: “My D.C. tour business was down 89%…”

In this week’s Failure Friday segment, we hear from a Washington, DC tour guide who loses nearly all of his side income due to COVID-19. 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 o...

May 28, 20215 minEp. 1609

#1608 - TBT: Diabetic Travel Blogger Embraces #VanLife

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an Irish travel blogger with type 1 diabetes. She’s recently moved to YouTube—and into a tiny home on wheels. 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 ...

May 27, 20219 minEp. 1608

#1607 - Q&A: How to best use a time of unemployment?

A listener who experiences a layoff has a severance package that lasts two months. In addition to looking for full-time work, how can he build another form of financial security during this 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]...

May 26, 20216 minEp. 1607

#1606 - Sports Cards Trading Hobby Becomes Pandemic Payday

When a perennial side hustler reconnects with his childhood hobby of sports trading cards, he brings in more than $20,000. 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: @ch...

May 25, 20218 minEp. 1606

#1605 - Q&A: What’s the best way to market a guide to airline lounges?

A listener wants to make an airline lounge access guide to help more people experience these magical places. What’s the best approach to creating and marketing 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: [email protected] Be on the show: SideHustleSch...

May 24, 20216 minEp. 1605

#1604 - French Bulldog Blog Fetches Extra Bones

After introducing a French bulldog into the family, a man finds a way to get paid blogging about 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: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect ...

May 23, 20216 minEp. 1604

#1603 - Q&A: How to become an affiliate manager for large launches?

Some product launches have an “affiliate manager” who coordinates promotion efforts. How can our listener offer this service on a freelance basis? 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 22, 20216 minEp. 1603

BONUS: Planning for a New Tomorrow, Part III

An asymmetrical opportunity is one where the risk is low but the possible reward is high. Starting a small business on a low budget is a perfect example: it might not work out, but if it does, there's no fixed limit to growth. In this series of short episodes from our partner Dell, I'll share three examples of how ordinary people are exploiting asymmetrical opportunities to radically transform their lives. The new tomorrow will not be televised–it's available on demand right now! Our final examp...

May 21, 20215 min

#1602 - Failure Friday: “I thought I had the Midas touch...”

In this week’s Failure Friday segment, we hear from a digital marketer who spends months creating a life-changing “killer app” that no one wants. 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 21, 20216 minEp. 1602

#1601 - TBT: Handbags for Active Women Goes Direct to Consumers

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Go Dash Dot, which sells handbags and other accessories for active women. 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...

May 20, 20219 minEp. 1601

#Ep. 1600 - Q&A: How to create a revenue stream not affected by Google?

We made it to #1,600! A listener’s product review site is starting well, but every day they see how dependent it is on the whims of Google search results. Can anything be done? 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 19, 20216 minEp. 1600

#1599 - Pastor Keeps the Faith with Clergy Subscription Boxes

A Lutheran pastor creates breathing room in her budget with a popular subscription box for fellow ministers. 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 ...

May 18, 20219 minEp. 1599

#1598 - Q&A: Why do online courses cost so much … or so little?

Online courses are everywhere! Some cost $20 and others cost $2,000 or more. Why is there no consistency in pricing—and how can you determine what *your* price should be? 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: SideHu...

May 17, 20216 minEp. 1598

#1597 - “Bee Man of New Jersey” Buzzes Into Money Hive

A beekeeper puts his bees to work, turning a hobby into a money-making hustle. Bee smart and listen to this episode! 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...

May 16, 20217 minEp. 1597

#1596 - Q&A: Should I use Etsy's new platform or build my own website?

A listener with an Etsy shop wants to open her own site as well. What’s the best way to branch 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: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect o...

May 15, 20216 minEp. 1596

BONUS: Planning for a New Tomorrow, Part II

An asymmetrical opportunity is one where the risk is low but the possible reward is high. Starting a small business on a low budget is a perfect example: it might not work out, but if it does, there's no fixed limit to growth. In this series of short episodes from our partner Dell, I'll share three examples of how ordinary people are exploiting asymmetrical opportunities to radically transform their lives. The new tomorrow will not be televised–it's available on demand right now! Our second exam...

May 14, 20214 min

#1595 - Failure Friday: “If it worked once, it should work twice… right?”

In this week’s Failure Friday segment, we hear from a full-time blogger who migrates to YouTube. His first attempt is a big win, so he assumes he can do it again—but that turns out to be a big assumption. 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@sidehustl...

May 14, 20217 minEp. 1595

#1594 - TBT: The 7-Figure Dachshund Apparel Business

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-founder of Bean Goods, which sells dachshund-themed apparel for dogs and humans. 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...

May 13, 20218 minEp. 1594

#1593 - Q&A: “I want to bet on The Bachelor…”

A listener wants to start an online marketplace where people bet on the outcome of The Bachelor. Millions of fans watch every week—is this a crazy 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/que...

May 12, 20215 minEp. 1593

#1592 - A Doggie Bag With a Twist

A Cleveland woman creates a dog walking accessory bag for active pet owners. Prototyping is ruff, but eventually she begins to paw-sper. 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 o...

May 11, 20217 minEp. 1592

#1591 - Q&A: Should I start a Substack newsletter?

Substack and other services that offer writers the chance to publish paid newsletters are getting a lot of attention. What do you need to know if you’d like to jump in? 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...

May 10, 20217 minEp. 1591

#1590 - Social Worker Finds Calm, Makes Cash with Business Course

A therapist and single mom earns extra income helping other therapists set up a private practice. 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 Connect on ...

May 09, 20217 minEp. 1590

#1589 - Q&A: Do I have to tell my customers where I'm based?

A listener in Europe wants to sell online, primarily to Americans. Do his customers need to know he’s overseas? 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: @chrisguillebe...

May 08, 20215 minEp. 1589