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

#2424 - First $1,000: The Med School “Decision Doctor”

In this week’s First $1,000 segment, we hear from a medical resident working in Chicago who has a side hustle as the med school “decision doctor,” helping students and interns navigate crucial decisions. 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...

Aug 21, 2023•7 min•Ep 2424•Transcript available on Metacast

#2423 - Q&A: “Do authors get paid for Kindle Unlimited books?”

Authors who publish books in the Kindle Unlimited (KU) program earn royalties based on the number of page views you receive—but parts of the process remain a mystery. Let’s help an aspiring author decide if KU is the best fit for him. 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...

Aug 20, 2023•6 min•Ep 2423•Transcript available on Metacast

#2422 - Q&A: “How to help businesses transition to cloud services?”

A caller in India has his sights set on the rapidly expanding field of cloud computing. What’s the best way to market a service targeted to small businesses? 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...

Aug 19, 2023•5 min•Ep 2422•Transcript available on Metacast

#2421 - Failure Friday: Bank Cancels TikTok Star’s Revenue Stream

In this week’s Failure Friday segment, we hear from an aspiring travel blogger and TikTok streamer. After an initial run at making a good income, the banking partner she worked with dropped her from its affiliate program. 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: ...

Aug 18, 2023•8 min•Ep 2421•Transcript available on Metacast

#2420 - TBT: Life Coaching Didn’t Work; This Was Better

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a coach who transformed from general life coaching (not a great business model!) to focusing more specifically on self-confidence. 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...

Aug 17, 2023•8 min•Ep 2420•Transcript available on Metacast

#2419 - Q&A: “How to set up a paid mastermind group?”

A “mastermind” of peers in your industry can be a free, informal group—or it can be a profit center for the right person. How would you set up one that makes 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: team@sidehustleschool.com Be on the show: SideHustleSchoo...

Aug 16, 2023•6 min•Ep 2419•Transcript available on Metacast

#2418 - Q&A: “Do you know of a Business Bootcamp?”

An engineer in Alberta wants to jumpstart his side hustle with a short “business bootcamp.” Does such a thing exist—and if not, might there be a 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...

Aug 15, 2023•6 min•Ep 2418•Transcript available on Metacast

#2417 - First $1,000: British Gaming Computer Navigates Brexit

In this week’s First $1,000 segment, we hear from a British university student who builds custom computers, selling them to gamers looking for an edge in the form of faster performance. 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 ...

Aug 14, 2023•7 min•Ep 2417•Transcript available on Metacast

#2416 - Q&A: “Get paid to take photos with Snappr…”

An amateur photographer signs up for Snappr, the service that describes itself as “Uber for photographers.” If you want to get paid to shoot portrait sessions, pay attention. 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: SideH...

Aug 13, 2023•6 min•Ep 2416•Transcript available on Metacast

#2415 - Q&A: “I HATE making sales calls…”

A software consultant is getting off to a good start with his side business, but he has one problem: he *strongly* dislikes making sales calls. Let’s see if we can help out our fellow introvert! 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 B...

Aug 12, 2023•6 min•Ep 2415•Transcript available on Metacast

#2414 - Failure Friday: Couples’ Intimacy Coach Fails to Spark Passion

In this week’s Failure Friday segment, we hear from an “up close and personal” intimacy coach for couples. Alas, her quest to become the Cupid of the digital age fizzled 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: SideH...

Aug 11, 2023•6 min•Ep 2414•Transcript available on Metacast

#2413 - TBT: Book Launch Manager Gets Paid to Pitch Authors

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a book launch manager who gets paid to pitch authors. Specifically, she helps upcoming and newly released books to get more attention … by any means necessary! 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: SideHustle...

Aug 10, 2023•6 min•Ep 2413•Transcript available on Metacast

#2412 - Q&A: “I’m making $10k/month … but I feel overwhelmed.”

This ecommerce business is taking off, but the owner isn’t sure what to do next. How do you handle an unexpected 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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisg...

Aug 09, 2023•6 min•Ep 2412•Transcript available on Metacast

#2411 - Q&A: “I’m ready to buy and sell sneakers!”

An MBA student wants to get in on sneaker reselling. Does he have what it takes to put his best foot forward? 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 Co...

Aug 08, 2023•5 min•Ep 2411•Transcript available on Metacast

#2410 - First $1,000: Electric Vehicle “Sherpa” Offers Fast Delivery

In this week’s First $1,000 segment, we hear from a guy operating an all-new side hustle: he helps electric vehicle buyers get their cars sooner! 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...

Aug 07, 2023•6 min•Ep 2410•Transcript available on Metacast

#2409 - Q&A: “Should I sell on eBay, Etsy, or Shopify?”

Selling on multiple platforms can increase revenue, but also generates more headaches. For a busy side hustler who can only be in one place at a time, how should you choose? 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: SideHu...

Aug 06, 2023•6 min•Ep 2409•Transcript available on Metacast

#2408 - Q&A: “An at-home escape room kit…”

Live from Ireland, this chemical engineer has a passion for puzzles and mind games—and she wants to sell an at-home escape room kit! How can we get this cool (yet constraining) idea unlocked? 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...

Aug 05, 2023•6 min•Ep 2408•Transcript available on Metacast

#2407 - Failure Friday: “Once I knew I had ADHD, everything made more sense…”

In this week’s Failure Friday segment, we hear from a self-employed programmer who struggled with motivation and procrastination. After many years of difficulty, he received an ADHD diagnosis that led to much improved habits. (I’ve been there! I have ADD, too.) 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. ...

Aug 04, 2023•7 min•Ep 2407•Transcript available on Metacast

#2406 - TBT: Georgia Fruit Stand Seller Sees Juicy Returns

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a fruit stand seller in Georgia. After three years of setting up shop, it now earns more than $50,000 a season. 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...

Aug 03, 2023•6 min•Ep 2406•Transcript available on Metacast

#2405 - Q&A: “Career coaching, live from Tokyo…”

A listener in Japan wants to leverage 15 years of cross-cultural experience into an online venture. 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 I...

Aug 02, 2023•5 min•Ep 2405•Transcript available on Metacast

#2404 - Q&A: “Help, I only have $100 to spend!”

A single mom from Detroit is ready to start side hustling, but only has $100 to spare. Is there anything she can do? (Short version: YES.) 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...

Aug 01, 2023•5 min•Ep 2404•Transcript available on Metacast

#2403 - First $1,000: Freelance Animator Makes Snappy Commercial Videos

In this week’s First $1,000 segment, we hear from a financial analyst with a secret side hustle making snappy short videos. 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: @chri...

Jul 31, 2023•6 min•Ep 2403•Transcript available on Metacast

#2402 - Q&A: “How does a gadget reviewer expand his platform?”

A tech enthusiast hopes to go from unboxing on YouTube to reaching more people on different platforms. 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 o...

Jul 30, 2023•5 min•Ep 2402•Transcript available on Metacast

#2401 - Q&A: “Am I too late to the side hustle party?”

Do you ever feel like you’re too late to something? That’s what this longtime school teacher is feeling. Good news: she’s *not* too late, and neither are you. 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/...

Jul 29, 2023•5 min•Ep 2401•Transcript available on Metacast

#2400 - Failure Friday: The Dial-a-Poem Hotline

In this week’s Failure Friday segment, we hear from a longtime poetry lover who offers a service called Dial-a-Poem: basically a personal poetry hotline. 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/quest...

Jul 28, 2023•7 min•Ep 2400•Transcript available on Metacast

#2399 - TBT: Hand Lettered Wedding Invites Are Here to Stay

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a retail associate who uses her calligraphy skill to start a side hustle offering hand-lettered wedding invitations. 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...

Jul 27, 2023•6 min•Ep 2399•Transcript available on Metacast

#2398 - Q&A: “Starting out in real estate in San Francisco…”

If you want to flip houses, is San Francisco really the best market? 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: @193countries Visit C...

Jul 26, 2023•5 min•Ep 2398•Transcript available on Metacast

#2397 - Q&A: “I’m ready to make an app! Uh, what should it be?”

Calling in from Seattle, Amy is a software developer who's been mulling over the idea of creating her own mobile app—but what kind of app should she make?? 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/que...

Jul 25, 2023•5 min•Ep 2397•Transcript available on Metacast

#2396 - First $1,000: Selling Vintage Clothes on Poshmark

In this week’s First $1,000 segment, we hear from a seller of vintage and modern clothes who uses the online marketplace Poshmark to sell thousands of dollars of clothes each 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 on the show...

Jul 24, 2023•7 min•Ep 2396•Transcript available on Metacast

#2395 - Q&A: “SEO consulting for small businesses…”

A digital marketing professional wants to start side hustling. How can he position himself to serve local businesses with SEO? 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: @c...

Jul 23, 2023•5 min•Ep 2395•Transcript available on Metacast