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

#2543 - First $1,000: Anime Artist Offers Personalized Commissions

In this week's First $1,000 segment, a talented artist capitalizes on their love for anime by offering personalized art commissions. Learn how they navigated pricing strategies, portfolio creation, and keeping up with 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 Em...

Dec 18, 2023•5 min•Ep 2543•Transcript available on Metacast

#2542 - Q&A: “Is SEO just a scam?”

It’s important to rank well in search engines—but can you really control such a thing? A listener wonders if the whole SEO industry is effectively a scam. 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...

Dec 17, 2023•5 min•Ep 2542•Transcript available on Metacast

#2541 - Q&A: “How to integrate masculine and feminine energy in my hustle?”

Is there room in the business world for non-traditional concepts like masculine and feminine energy, and how might this differentiate a 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 ...

Dec 16, 2023•5 min•Ep 2541•Transcript available on Metacast

#2540 - Failure Friday: Profitable Affiliate Website Peters Out

In this week’s Failure Friday segment, we explore the downfall of a once-lucrative affiliate business. Tune in to uncover how a stubborn mindset led to a financial nosedive—and the crucial pivot that followed. 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...

Dec 15, 2023•7 min•Ep 2540•Transcript available on Metacast

#2539 - TBT: Organizational Advisor Moves from B2C to B2B

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an organizational advisor who starts with home consultations, but transitions to serving businesses when she spots high demand. 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...

Dec 14, 2023•5 min•Ep 2539•Transcript available on Metacast

#2538 - Q&A: “How can I sell my big app idea?”

Like the idea of making an app, then selling it for millions? Don’t miss 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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @19...

Dec 13, 2023•5 min•Ep 2538•Transcript available on Metacast

#2537 - Q&A: “When’s the best time to start??”

A caller is wondering about the optimal time to start a side hustle. Does such a thing exist? 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 Instagr...

Dec 12, 2023•5 min•Ep 2537•Transcript available on Metacast

#2536 - First $1,000: Vintage Luggage Upcycler Hits Ground Running

In this week's First $1,000 segment, an upcycler transforms forgotten vintage luggage into functional art pieces. 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: @chrisguillebea...

Dec 11, 2023•5 min•Ep 2536•Transcript available on Metacast

#2535 - Q&A: “How can I repurpose content from YouTube?”

Creating content is time-consuming. How can you repurpose your content to fit multiple platforms without doubling your workload? 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: ...

Dec 10, 2023•6 min•Ep 2535•Transcript available on Metacast

#2534 - Q&A: “Should I accept ads from pharmaceutical companies?”

Is it ethical for a health-focused podcast to accept sponsorships from online therapy and pharmaceutical companies? 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: @chrisguilleb...

Dec 09, 2023•6 min•Ep 2534•Transcript available on Metacast

#2533 - Failure Friday: Working Remotely from Thailand Is Stressful!

In this week’s Failure Friday segment, we hear from a software engineer who takes advantage of his company’s flexible remote work policy to move to Thailand—but struggles in adapting to working in the middle of the night. 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: ...

Dec 08, 2023•7 min•Ep 2533•Transcript available on Metacast

#2532 - TBT: The Shine and Rise of an Office Cleaning Maven

In this week’s “Throwback Thursday / Where are they now?” segment, we explore the evolution of a Minneapolis-based office cleaning service that polished its approach to staffing, customer retention, and sustainability. 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: tea...

Dec 07, 2023•6 min•Ep 2532•Transcript available on Metacast

#2531 - Q&A: “Can I use ChatGPT to help with social media?”

How can AI technology be used effectively for creating a constant stream of engaging social media 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 show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Conne...

Dec 06, 2023•5 min•Ep 2531•Transcript available on Metacast

#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, 2023•5 min•Ep 2530•Transcript available on Metacast

#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, 2023•5 min•Ep 2529•Transcript available on Metacast

#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, 2023•6 min•Ep 2528•Transcript available on Metacast

#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, 2023•5 min•Ep 2527•Transcript available on Metacast

#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, 2023•7 min•Ep 2526•Transcript available on Metacast

#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, 2023•5 min•Ep 2525•Transcript available on Metacast

#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, 2023•5 min•Ep 2524•Transcript available on Metacast

#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, 2023•5 min•Ep 2523•Transcript available on Metacast

#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, 2023•6 min•Ep 2522•Transcript available on Metacast

#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, 2023•5 min•Ep 2521•Transcript available on Metacast

#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, 2023•5 min•Ep 2520•Transcript available on Metacast

#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, 2023•7 min•Ep 2519•Transcript available on Metacast

#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, 2023•7 min•Ep 2518•Transcript available on Metacast

#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, 2023•7 min•Ep 2517•Transcript available on Metacast

#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, 2023•6 min•Ep 2516•Transcript available on Metacast

#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, 2023•7 min•Ep 2515•Transcript available on Metacast

#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, 2023•5 min•Ep 2514•Transcript available on Metacast