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

#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, 20235 minEp. 2411

#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, 20236 minEp. 2410

#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, 20236 minEp. 2409

#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, 20236 minEp. 2408

#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, 20237 minEp. 2407

#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, 20236 minEp. 2406

#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, 20235 minEp. 2405

#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, 20235 minEp. 2404

#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, 20236 minEp. 2403

#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, 20235 minEp. 2402

#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, 20235 minEp. 2401

#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, 20237 minEp. 2400

#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, 20236 minEp. 2399

#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, 20235 minEp. 2398

#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, 20235 minEp. 2397

#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, 20237 minEp. 2396

#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, 20235 minEp. 2395

#2394 - Q&A: “Should I become a financial advisor for healthcare workers?”

Today’s caller works as a data analyst in the health sector, but she's also got a keen interest in investing. Might there be a way to combine these talents for one side hustle to rule them all? 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...

Jul 22, 20235 minEp. 2394

#2393 - Failure Friday: Ghost Tours Fail to Scare Enough Clients

In this week’s Failure Friday segment, we hear a spooky story: an attempt at offering a ghost tour of Denver fails to scare enough people into signing 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: SideHustleSchool.com/ques...

Jul 21, 20236 minEp. 2393

#2392 - TBT: Game Consoles, VCRs, and Typewriters for Sale

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a reseller who specializes in retro electronics including vintage game consoles and typewriters. 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: Sid...

Jul 20, 20236 minEp. 2392

#2391 - Q&A: “How to sell a ‘Democracy in Action’ program?”

A listener looking to inspire others to become more active in their local government wants to start a subscription service of some kind. 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 T...

Jul 19, 20236 minEp. 2391

#2390 - Q&A: “Can I tell someone else’s story on my podcast?”

If you make a storytelling podcast, can you tell someone else’s story without their permission? 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 Insta...

Jul 18, 20235 minEp. 2390

#2389 - First $1,000: Indian Tutor Helps U.S. High School Students Learn Math

In this week’s First $1,000 segment, we hear from an Indian listener. He’s built a bustling business as an online math tutor for high school students in the U.S. 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...

Jul 17, 20236 minEp. 2389

#2388 - Q&A: “What should I sell on Fiverr?”

A digital nomad with a range of skills wants to offer services on Fiverr. How should he specialize to be most efficient and profitable? 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 Tw...

Jul 16, 20236 minEp. 2388

#2387 - Q&A: “It’s hard to compete with bigger firms!”

A talented designer is facing competition with larger design firms in her area. How can she stand out and make her mark? 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: @chrisgu...

Jul 15, 20235 minEp. 2387

#2386 - Failure Friday: Homemade Hummus Subscription Fails to Smash

In this week’s Failure Friday segment, we hear from a listener with a tangy idea. Drawing on her Lebanese ancestry, she tries to create a “homemade hummus subscription box. Alas, those chickpeas failed to smash themselves into a hit. 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...

Jul 14, 20237 minEp. 2386

#2385 - TBT: Project Manager Side Hustles as Home Inspector

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a project manager in the construction industry who has a side hustle as a home inspector. This second job earns several thousand dollars a 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 Ema...

Jul 13, 20236 minEp. 2385

#2384 - Q&A: “How to use the Pomodoro method in my side hustle?”

The Pomodoro method is a classic productivity tool. How can this listener—or anyone—use it when building their 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: SideHustleSchool.com/questions Connect on Twitter: @chri...

Jul 12, 20236 minEp. 2384

#2383 - Q&A: “Need help attracting first clients…”

A sales coach for Etsy and Shopify sellers is looking to expand her initial client base of friends and family members. 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: @chrisguil...

Jul 11, 20235 minEp. 2383

#2382 - First $1,000: Airbnb Marketer Increases Rental Rates 30%

In this week’s First $1,000 segment, we hear from a guy who helps Airbnb property owners and managers grow their listings and revenue. 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 Twi...

Jul 10, 20236 minEp. 2382
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