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

#2530 - Q&A: “How can I transition from corporate to career coaching?”

A listener with over ten years of experience in corporate leadership is looking to transition into career coaching. What are the essential steps he needs to take to make this career shift a successful one? 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@sidehustles...

Dec 05, 20235 minEp. 2530

#2529 - First $1,000: Data Specialist Whips Up Custom Reports

In this week’s First $1,000 segment, we hear from a freelance data visualization expert who turned indecipherable data into compelling narratives. 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 Co...

Dec 04, 20235 minEp. 2529

#2528 - Q&A: “My ADHD makes side hustling hard…”

A listener with ADHD is struggling to keep a photography side hustle on track. If you identify as neurodivergent, how can you adjust your productivity strategy? 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...

Dec 03, 20236 minEp. 2528

#2527 - Q&A: “An online course for teaching ‘Uncommon Skills…’”

Ever thought of turning niche hobbies like unicycling or yo-yo tricks into an online course? That’s what today’s listener has in mind. 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...

Dec 02, 20235 minEp. 2527

#2526 - Failure Friday: He Bought a ‘Bored Ape’ NFT for $80,000

In this week’s Failure Friday segment, we hear from an eager enthusiast of digital art. He bought a popular “bored ape” NFT for a *lot* of money—then watched as the value dropped by 80%. 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...

Dec 01, 20237 minEp. 2526

#2525 - TBT: Electronic Music Producer Offers Lessons & Mentorship

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an electronic music producer who also coaches other musicians. 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 Connec...

Nov 30, 20235 minEp. 2525

#2524 - Q&A: “Is it too late to plan for holiday sales?”

An eCommerce store owner is concerned she's a bit late to leverage the traditional fourth-quarter sales spike. Is it a lost cause? 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...

Nov 29, 20235 minEp. 2524

#2523 - Q&A: “A service to help small museums with social media…”

Today's caller wants to use her love for art and history to help small museums and galleries improve their social media presence and, in turn, boost visitor numbers. How can she structure this passion into a viable 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 E...

Nov 28, 20235 minEp. 2523

#2522 - First $1,000: Birth Chart Consults Aim for Stars

In this week’s First $1,000 segment, we hear from a digital age astrologer who sells personalized birth charts, charting the stars for her clients. 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 C...

Nov 27, 20236 minEp. 2522

#2521 - Q&A: “Are my Kindle highlights hiding a business opportunity?”

How can you manage your Kindle highlights—and is there a business opportunity lurking in this common challenge? 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 ...

Nov 26, 20235 minEp. 2521

#2520 - Q&A: “My enthusiasm fizzles out…”

A listener finds himself losing interest in side hustling after an initial burst of enthusiasm. What should you do when your early ideas keep fizzling 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: SideHustleSchool.com/que...

Nov 25, 20235 minEp. 2520

#2519 - Failure Friday: Financial Abundance Coach Charges Too Much

In this week’s Failure Friday segment, we hear from a woman who sets out to become a financial abundance coach—but prices her online course too high for her initial clients. 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...

Nov 24, 20237 minEp. 2519

#2518 - TBT: Blankets from Nepal Continue to Sell

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a U.K. importer of cashmere blankets. Two years after starting her business, it’s going stronger than ever! 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 th...

Nov 23, 20237 minEp. 2518

#2517 - Q&A: “What are average affiliate commission rates?”

How much can you get paid to promote other people’s products? A listener wants to know about the average rates for affiliate commissions. 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 ...

Nov 22, 20237 minEp. 2517

#2516 - Q&A: “Can you earn a big DoorDash bonus and then quit?”

Chasing after sign-up bonuses in the gig economy can seem like a quick way to boost earnings. It’s not a longterm income source, but once in a while it’s worth 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...

Nov 21, 20236 minEp. 2516

#2515 - First $1,000: Paralegal Assists U.S. Immigrants to Canada

In this week’s First $1,000 segment, we hear from a Canadian paralegal who helps American immigrants learn to navigate the bureaucracy of migration. 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 ...

Nov 20, 20237 minEp. 2515

#2514 - Q&A: “My membership site has a high churn rate…”

A fitness trainer is grappling with a high churn rate in their membership-based business, compounded by burnout. How can they improve retention? 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 Conn...

Nov 19, 20235 minEp. 2514

#2513 - Q&A: “A personal stylist for remote workers…”

A listener wants to help remote workers look good on screen. Can she monetize her passion for “Zoom fashion”? 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...

Nov 18, 20235 minEp. 2513

#2512 - Failure Friday: PayPal Freezes $50,000 in Ticket Fees

In this week’s Failure Friday segment, we hear from a first-time event host who sells out a big event—only to discover that PayPal refuses to give him the money. Lots of lessons here! 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...

Nov 17, 20238 minEp. 2512

#2511 - TBT: The Midwest Car Parts Mogul

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a car parts reseller in Missouri who’s been growing his side hustle all the way to six-figures. What can we learn from his story? 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@sidehus...

Nov 16, 20235 minEp. 2511

#2510 - Q&A: “It’s time to sell my website… how do I do it??”

Selling a passion project website can be an emotional journey. Today, we navigate the steps of valuating and selling a site while ensuring it remains in capable and caring hands. 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: S...

Nov 15, 20235 minEp. 2510

#2509 - Q&A: “Can you still profit from blockchain video games?”

Ever wondered if playing video games could actually make you money? Today, we look into the world of blockchain video games and assess if they can still be a profitable 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...

Nov 14, 20235 minEp. 2509

#2508 - First $1,000: Video Editor Upgrades from Low-Paying Clients

In this week’s First $1,000 segment, we hear from a video editor who starts taking cheap gigs on Fiverr before moving up to serving more valuable clients. 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...

Nov 13, 20237 minEp. 2508

#2507 - Q&A: “Should I be a Creator or an Influencer … or neither?”

Are you a creator, an influencer, or perhaps a bit of both? Today's listener is curious about the difference between these frequently-used terms 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 Conn...

Nov 12, 20235 minEp. 2507

#2506 - Q&A: “Does Peak Marketplace mean we’ve reached a saturation point?”

Have we hit 'Peak Marketplace,' a point where the online world is too crowded for new entrepreneurs? This caller brings up an alternative perspective to a point I made in Gonzo Capitalism. 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 t...

Nov 11, 20234 minEp. 2506

#2505 - Failure Friday: “Remote Year” Nomad Experiences Blogger Burnout

In this week’s Failure Friday segment, we hear from a digital nomad who sets out to travel for a year—but soon becomes overwhelmed at the idea of building a business on the road. 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: S...

Nov 10, 20238 minEp. 2505

#2504 - TBT: Las Vegas Concierge Sells Subscriptions & Savings

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Vegas local who helps tourists save on their visits to Sin City. This is a profitable business for her, bringing in up to $5,000/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 E...

Nov 09, 20237 minEp. 2504

#2503 - Q&A: “I want to help gamers get fit…”

Can you merge the worlds of fitness and gaming into a unique side hustle? Our caller today is a certified trainer looking to tailor workout routines for gamers. Let’s see if we can help him level-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....

Nov 08, 20235 minEp. 2503

#2502 - Q&A: “What’s the deal with #BookTok?”

What's the business model behind viral book trends on social media like #bookstagram and #BookTok? This listener wants to understand how creators are monetizing book-related content. 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 sho...

Nov 07, 20235 minEp. 2502

#2501 - First $1,000: The Canadian Wilderness Experience Curator

1 In this week’s First $1,000 segment, we hear from an Alberta man who leads hikes and tours to wilderness areas in his province, incorporating indigenous knowledge and local sites. 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...

Nov 06, 20235 minEp. 2501
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