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.
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Start out on the Right Foot! Real Estate Side Hustle Skool: https://www.skool.com/realsidehustle/about Real Estate Side Hustle Skool is a comprehensive training program designed to equip active duty military, veterans, and their spouses - and anyone else - with the knowledge and skills needed to succeed in the real estate industry. The program offers two distinct pathways: the Passive Agent Pathway, which focuses on generating income through real estate referrals, and the Active Agent Pathwa ...
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TBT: Building a Range of Productivity Tools
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#block-110dc8b2 h2 { width: 401px; } What It’s About This smart seller has learned to make productivity tools that people want to buy. Notes from Chris Episode 2819 Welcome to Throwback Thursday / “Where are they now?” where we take an in-depth look at someone who’s story has evolved considerably since we first featured them. Last week, we heard fr…
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#2819 - TBT: Building a Range of Productivity Tools
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In this week’s “Throwback Thursday” segment, we hear from a seller of productivity guides who has evolved his business over the years. Discover how he transitioned from a single popular guide and now sells a range of products, earning over $100,000 a year. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of peopl…
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Q&A: “My subscribers are paying for nothing…”
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#block-984a0508 h2 { width: 401px; } What It’s About An interesting dilemma from a newsletter publisher. Notes from Chris Episode 2818 Today’s question comes from Rachel in Baltimore, Maryland. She started a subscription-based newsletter last year and got 50 signups, but recently she’s been struggling to deliver the promised value to her subscriber…
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#2818 - Q&A: “My subscribers are paying for nothing…”
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In this episode, we explore how to handle the ethical dilemma of charging subscribers without fully delivering a service. What do you do if you stop providing something—but buyers keep paying?? 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, t…
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Q&A: “How can I identify and develop side hustle skills?”
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#block-8704d1f2 h2 { width: 401px; } What It’s About How do you discover your most profitable side hustle skills? Notes from Chris Episode 2817 Welcome back to Side Hustle School! Today’s question comes from Thomas, who’s been inspired by all the amazing side hustles featured on the podcast but feels uncertain about his own skills and where to begi…
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#2817 - Q&A: “How can I identify and develop side hustle skills?”
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This listener needs help discovering his skills! In this episode, we discuss how ANYONE can identify and develop skills for a successful 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 lis…
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First $1,000: Nashville Branding Agency Gets Personal
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#block-39a57131 h2 { width: 401px; } What It’s About This duo is serious about PR and branding. Notes from Chris Episode 2816 Today’s episode is part of a feature we call ‘Your First $1,000.’ As you might surmise from the title, this is all about how someone made their first $1,000. How did they get to that point? Not their first $100,000—that’s co…
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#2816 - First $1,000: Nashville Branding Agency Gets Personal
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In this week’s “First $1K” segment, we hear from a tag-team duo in Nashville who starts a personal branding agency. Discover how they earned their first $1,000 by helping entrepreneurs and influencers build their personal brands through digital marketing. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people…
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Q&A: “Should I get an expensive booth at a trade show?”
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#block-d4afaedb h2 { width: 401px; } What It’s About When is a trade show booth worth it? Notes from Chris Episode 2815 Welcome back to Side Hustle School! Today’s question comes from Marcus in Dallas. He’s considering getting a booth at a major trade show to showcase his products but is concerned about the high cost and whether it’s worth the inve…
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#2815 - Q&A: “Should I get an expensive booth at a trade show?”
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In this episode, we explore the factors to consider when deciding whether to invest in a trade show booth. These booths don’t come cheap … are they 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…
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Q&A: “How can I turn organizational skills into a business?”
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#block-57a5c2d2 h2 { width: 401px; } What It’s About She’s got skills—how can she profit from them? Notes from Chris Episode 2814 Welcome back to Side Hustle School! Today’s question comes from Melissa in Nashville. She has a knack for home organization and has helped friends and family declutter their spaces. Melissa is now considering turning thi…
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#2814 - Q&A: “How can I turn organizational skills into a business?”
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In this episode, we explore how to turn organizational skills into a profitable consulting service. Learn how to define your niche, build a portfolio, and market your services to attract clients and grow your business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quittin…
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Failure Friday: IP Complaint Ends Anime T-Shirt Venture
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#block-adda8372 h2 { width: 401px; } What It’s About Sadly, these t-shirts sold well—too well. Notes from Chris Episode 2813 I believe we can learn as much from failure as we can from success, if not more. It’s with this principle in mind that I offer you a weekly segment called Failure Friday: a collection of short stories all about mistakes, miss…
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#2813 - Failure Friday: IP Complaint Ends Anime T-Shirt Venture
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In this week’s “Failure Friday” segment, we hear from an enterprising seller who faced a setback when their anime-themed T-shirts were de-listed after an IP owner filed a complaint. 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 incl…
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TBT: Aquarium Maintenance Business Makes Splash
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#block-adbe8416 h2 { width: 401px; } What It’s About This fishy business earns legit income! Notes from Chris Episode 2812 Welcome to Throwback Thursday / “Where are they now?” where we take an in-depth look at someone who’s story has evolved considerably since we first featured them. Last week, we heard from a gaming Twitch streamer who discovered…
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#2812 - TBT: Aquarium Maintenance Business Makes Splash
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In this week’s “Throwback Thursday” segment, we hear from an Ohio man who turned his experience with aquariums into a maintenance service for homes and offices. 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 less…
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Q&A: “Creative ways to monetize a property rental…”
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#block-11e9377b h2 { width: 401px; } What It’s About What are some ways to monetize a property rental—besides Airbnb? Notes from Chris Episode 2811 Welcome back to Side Hustle School! Today’s question comes from Lucia, who I had the pleasure of meeting at a recent event. She owns a property and is looking for creative ways to monetize it beyond the…
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#2811 - Q&A: “Creative ways to monetize a property rental…”
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In this episode, we explore creative ways to monetize a property rental beyond Airbnb. We’ll consider event rentals, setting up a co-working space, or even urban farming to maximize a property’s potential. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. …
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Q&A: “How can I monetize my drone piloting skills?”
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#block-3add215e h2 { width: 401px; } What It’s About This drone pilot has skills, but no business model. Notes from Chris Episode 2810 Today’s question comes from Jake in San Diego. He recently got his drone pilot license and is passionate about flying drones as a hobby. Jake is curious about how to monetize his drone skills and is eager to learn a…
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#2810 - Q&A: “How can I monetize my drone piloting skills?”
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In this episode, we explore how to get paid for drone piloting. That’s right—drone skills are valuable! 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: …
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#2809 - First $1,000: Coffee Cart Business Brews Up Baltimore
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In this week’s “First $1K” segment, we hear from an aspiring entrepreneur in Baltimore who starts a seasonal pop-up coffee cart. 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 day…
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#2808 - Q&A: “How can we improve a non-profit membership drive?”
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In this episode, we explore effective strategies to improve a non-profit membership drive. Learn how to attract more members and ensure growth with actionable tips and insights. 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…
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#2807 - Q&A: “Should I write for Forbes for free?”
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In this episode, we critically examine the pros and cons of writing for a prestigious platform like Forbes without getting paid. Discover whether the potential benefits truly outweigh the significant downsides. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their …
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#2806 - Failure Friday: Coder’s App Flops on Product Hunt
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In this week’s “Failure Friday” segment, we hear from a hacker who develops an app to solve a common coding problem, but launches before conducting proper market research. Oops! Back to the drawing board. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. T…
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#2805 - TBT: A Gamer’s Journey from Twitch to YouTube
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In this week’s “Throwback Thursday” segment, we hear from a gaming Twitch streamer who discovered he could make more money by uploading popular streams to YouTube. Learn how he optimized his content for both platforms. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quittin…
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#2804 - Q&A: “Turning a viral video into income…”
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In this episode, we discuss how to turn viral fame into a potential income stream. Can one big video create an all-new career? 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 …
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#2803 - Q&A: “Once you make a game or app, how can you distribute it?”
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In this episode, we explore how to distribute a new game or app effectively. Once you’ve made it—how can you get it in the hands of as many players as possible? 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 less…
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#2802 - First $1,000: Turning Passion into Profit with Fantasy Maps
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In this week’s “First $1K” segment, we hear from an artist who turned their passion for creating fantasy maps into a profitable business. Discover how they earned their first $1,000 by selling custom maps to tabletop gamers and fantasy authors. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn e…
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#2801 - Q&A: “How can I sell clothes on Depop?”
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In this episode, we explore tips for successfully selling on Depop and why it’s become so popular with a younger audience. Learn how to make your listings stand out and attract buyers in this trendy marketplace. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their…
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#2800 - Q&A: “How does anyone profit on Temu?
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In our 2,800th episode (!), we explore how to succeed on the competitive marketplace of Temu. Learn about selecting the right products, creating standout listings, and leveraging marketing techniques to boost your sales. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitt…
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