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

Ep. 3062 - Q&A: “Are there any ‘good’ MLMs?”

Are there any ‘good’ MLMs, or are they all a bad idea? In this episode, we break down the truth about multi-level marketing and why it’s rarely a smart 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: [email protected] Be on the sho...

May 20, 20254 minEp. 3062

Ep. 3061 -First $1,000: Coffee Gear Affiliate Site Brews Profits

In this week’s First $1,000 story, learn how one coffee enthusiast brewed up an SEO-driven affiliate strategy, hitting $1,000 by offering thoughtful gear recommendations. 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: Sid...

May 19, 20257 minEp. 3061

Ep. 3060 - Weekend Workshop: Burn Down the Furniture Store

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: why you should ‘burn down the furniture store,’ AKA the power of special offers. 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 gu...

May 18, 20257 minEp. 3060

Ep. 3059 - Q&A: “How can I wireframe a website?”

How do you wireframe a website without getting lost in the details? In this episode, we break down the best tools and strategies to map out your website idea before you build. 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: Side...

May 17, 20255 minEp. 3059

Ep. 3058 - Q&A: “Is it a good time to launch a meme coin?”

Are crypto meme coins a viable side hustle, or are they just a fast track to failure? We break down the risks, rewards, and what it takes to launch a meme coin that actually lasts. 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 16, 20255 minEp. 3058

Ep. 3057 -TBT: Crossing Borders, Boosting Orders

In this week’s “Throwback Thursday” segment, learn how a Canadian ecommerce expert turned his experience running an FBA shop into a consulting business, helping fellow Canadian sellers break into the lucrative U.S. 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: SideHustl...

May 15, 20257 minEp. 3057

Ep. 3056 - STORY: Architect Creates Mini-Blind Repair Too

It takes a long time to get to market, and success doesn’t come cheap—but this mini-blind “prescription” now earns an extra $15,000 a year for its inventor.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 14, 20259 minEp. 3056

Ep. 3055 - Q&A: “Can you really publish a book in a week?”

Can you really write and publish a book in just one week?  In this episode, we explore whether speed-publishing is realistic—or just a recipe for creating low-quality 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: [email protected] Be on the...

May 13, 20255 minEp. 3055

Ep. 3054 - First $1,000: Community Host Boosts Engagement and Retention

In this week’s First $1,000 story, learn how a personal touch and organized virtual events enabled one community manager to surpass the $1,000 mark while fostering a supportive space for solopreneurs. 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@sidehustle...

May 12, 20256 minEp. 3054

Ep. 3053 - Weekend Workshop: Test, Test, and Test Again

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: testing! 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: SideHustleScho...

May 11, 20257 minEp. 3053

Ep. 3052 - Q&A: “How can I push past hesitation and market my creative work?”

In today’s episode, we help a listener overcome self-doubt and fear of judgment while launching a creative business. Learn how to build confidence and connect with the right audience. 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 ...

May 10, 20255 minEp. 3052

Ep. 3051 - Q&A: “How do I balance what I love with what the market wants?”

Is it better to focus on what sells or what you love making? In this episode, we explore how to balance passion and profit in a product-based business. 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/questio...

May 09, 20254 minEp. 3051

Ep. 3050 - TBT: Lawn Sign Biz Expands to Wedding Décor Rentals

This week’s Throwback Thursday feature tells the story of a third-grade teacher who grew her creative lawn sign business into a go-to source for wedding décor. 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: SideHus...

May 08, 20255 minEp. 3050

Ep. 3049 - STORY: Internet Trolls Eat Their Words In This Comedic Cake Hustle

After seeing a mean comment on Dolly Parton’s Facebook page, a woman realizes the absurdity of internet trolling and bakes up a hilarious and ironic 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: [email protected] Be on the show: SideHustleSc...

May 07, 20257 minEp. 3049

Ep. 3048 - Q&A: “Best practices for Meta ads?”

Are Meta ads worth the investment? In this episode, we explore the best practices for running profitable campaigns on Facebook and Instagram in 2025. 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 06, 20255 minEp. 3048

Ep. 3047 - First $1,000: Pop-Up Cosplay Salon Takes Con-Goers by Surprise

In this week’s First $1,000 story, discover how a Seattle hairstylist unofficially sets up shop near comic conventions—charging cosplayers for last-minute wig rescues and hair touch-ups. 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 05, 20257 minEp. 3047

Ep. 3046 - Weekend Workshop: Ask 10 People for Help

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: building your support network. 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...

May 04, 20257 minEp. 3046

Ep. 3045 - Q&A: “Should I switch my business to a subscription model?”

Is switching to a subscription model the right move for your business? In this episode, we explore the pros, cons, and strategies for making the transition without alienating your customers. 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...

May 03, 20255 minEp. 2045

Ep. 3044 - Q&A: “Why do authors offer pre-order bonuses?”

Why do so many authors offer pre-order bonuses? In this episode, we explore whether these perks drive sales or just create extra work—and how to decide if they’re right for your book launch. 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@sidehustlescho...

May 02, 20256 minEp. 3042

Ep. 3043 - TBT: From Cracked Screens to Tech Buyback Business

In this week’s “Throwback Thursday” segment, we hear from a college student who scaled from fixing cracked screens to creating a buyback platform that turns over $20,000 in inventory 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@side...

May 01, 20256 minEp. 3043

Ep. 3042 - STORY: Fashion Buyer Creates Quirky Comfort Craze

Kyle Bergman has always had a unique and edgy taste in fashion. Then, thanks to one viral Buzzfeed article, he was able to create a brand that appeals to other people like 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: SideHustleSchool.com Email: [email protected] Be on the show: Sid...

Apr 30, 20256 minEp. 3042

Ep. 3041 - Q&A: “Should I expand the services I offer?”

How do you decide which new opportunities to pursue without overloading yourself? In this episode, we help a listener navigate expanding their business while staying focused and strategic. 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 t...

Apr 29, 20255 minEp. 3041

Ep. 3040 - First $1,000: Flipping Phones and Tablets for Fun and Profit

In this week’s First $1,000 segment, see how a simple promise of secure data wiping and refurbishment helped a tech-savvy neighbor earn thousands of dollars by flipping outdated electronics. 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]...

Apr 28, 20256 minEp. 3038

Ep. 3039 - Weekend Workshop: Sell Like a Girl Scout

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: the art of natural selling! 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 no...

Apr 27, 20256 minEp. 3039

Ep. 3038 - Q&A: “When is it worth spending money on your side hustle?”

When is it time to start spending real money on your side hustle? In this episode, we explore how to balance scrappiness with strategic investments to fuel growth. 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...

Apr 26, 20256 minEp. 3038

Ep. 3037 - Q&A: “How do I turn being an industry outsider into an advantage?”

How do you turn being an industry outsider into a strength? In this episode, we explore how to practice creativity while building trust and credibility with customers. 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: SideHustleSc...

Apr 25, 20254 minEp. 3037

Ep. 3036 - TBT: Montana Videographer Redefines Remote Filming

In this week’s Throwback Thursday segment, discover how a pro videographer ditched travel hassles by mailing filming kits worldwide and directing online course shoots entirely from afar. 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 ...

Apr 24, 20256 minEp. 3036

Ep. 3035 - STORY: Frozen Yogurt Dog Treats Are No Barking Matter

A Colorado couple creates a side hustle that gives dogs and their owners a way to enjoy their frozen treats from their own bowls. 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 Instagra...

Apr 23, 20256 minEp. 3035

Ep. 3034 - Q&A: “How can I incorporate activism into my brand without seeming performative?”

How do you build a business that aligns with your values without coming across as performative? In this episode, we help a listener navigate authenticity in sustainability and activism. 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 ...

Apr 22, 20255 minEp. 3034

Ep. 3033 - First $1,000: Feeding the Neighborhood, One Block at a Time

In this week’s First $1,000 segment, learn how a backyard gardener in Brooklyn joined forces with neighbors to create hyper-local produce boxes, quickly earning $1,000 with minimal overhead. 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]...

Apr 21, 20256 minEp. 3033
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