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Side Hustle School

Chris Guillebeau / Onward Project

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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 http ...
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Indie Film Hustle is dedicated to showing you how to hack filmmaking & the film business. Interviews with Acadamy Award® / Oscar nominees and industry professionals giving you the real deal from the inside with no BS, just the truth on what it takes to survive and thrive doing what you love. We discuss cinematography, RED Camera, Arri Alexa, Blackmagic camera, post production, color grading, filmmaking, visual effects, motion graphics, film festivals, editing, film crews, directing, producin ...
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In this episode, we explore how service-based businesses can guide clients through providing accurate information. Learn how to reduce costly mistakes and protect your 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…
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#block-d361eda1 h2 { width: 401px; } What It’s About How do we know what’s even real anymore? Notes from Chris Episode 3002 The rise of AI has made content creation easier but also more impersonal. For bloggers, writers, and creators, it can feel like you’re competing against a flood of automated material that’s everywhere online. Today’s question …
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In today’s episode, we tackle a growing concern for creators: how to stand out in a world increasingly dominated by AI-generated content. If you’re worried about keeping your work authentic and engaging, you’re not alone. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quit…
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#block-980ddc4b h2 { width: 401px; } What It’s About A little food blog grows up! Notes from Chris Episode 3001 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 test prep tutor who goes from juggling individua…
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In this week’s Throwback Thursday segment, learn how a recipe blogger moved beyond one-off cookbook sales to form a culinary community, offering seasonal meal plans, live demos, and valuable kitchen tool discounts. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting th…
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#block-eb3034cf h2 { width: 401px; } What It’s About The benefits of getting locked out of your apartment at night. Notes from Chris Episode 3000 In today’s story… How does a software engineer create a tiny, simple tool that fits in your wallet and goes on to sell more than 500,000 units? It earns $50,000 in its first year, and within a few years t…
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After getting locked out of his apartment, a software engineer creates a pocket tool that goes on to sell 500,000 units and employ 17 people. 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&…
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#block-fe5b4696 h2 { width: 401px; } What It’s About Neurodivergent-friendly ways to stay somewhat organized. Notes from Chris Episode 2999 Balancing a side hustle with a full-time job is no easy feat, especially when your to-do list keeps growing faster than you can cross things off. Today’s question comes from a nurse and side hustler who’s feeli…
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In today’s episode, we explore neurodivergent-friendly strategies to tackle an overwhelming to-do list. Learn how to work with your energy, build momentum, and stay productive without burnout. 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, th…
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#block-38c64559 h2 { width: 401px; } What It’s About Some people are willing to pay a lot of money for a home bar…. Notes from Chris Episode 2998 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 firs…
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In this week’s First $1,000 segment, discover how a Malibu bartender began designing home bars, added a line of custom bar tools, and launched virtual cocktail classes to reach $150,000 a year. 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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#block-e7063554 h2 { width: 401px; } What It’s About Today’s episode comes from Day 11, which is all about deciding on the best possible price for your offer. Notes from Chris Episode 2997 It’s Weekend Workshop, and it’s new! Listen to today’s episode to learn more… SEE ALSO: Catholic Designer Creates Stylish Apparel Line: What shall it profit a ma…
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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: finding the right price. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money …
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#block-08d39c76 h2 { width: 401px; } What It’s About Is this a great idea—or a great way to get sued? Notes from Chris Episode 2996 Starting a business with nostalgic appeal can be a great way to tap into a passionate audience. But when it comes to using images of celebrities, even those who have passed away, the legal landscape can get complicated…
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In today’s episode, we help an aspiring side hustler navigate the tricky world of copyright and likeness rights. Can you legally sell products featuring old-school celebrity images? Let’s break it down. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Thi…
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#block-a62d562d h2 { width: 401px; } What It’s About Is there a good—and easy—way to keep track of sales leads? Notes from Chris Episode 2995 Managing leads and client inquiries can be one of the biggest challenges for a growing business—especially when your inbox is bursting and sticky notes aren’t cutting it anymore. Today’s question comes from a…
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In this episode, we help a small business owner organize client leads without getting overwhelmed. Learn simple, affordable ways to track inquiries, follow-ups, and deadlines—even if you’re not ready for a big CRM system. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quit…
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#block-dbe0ff0b h2 { width: 401px; } What It’s About One-to-one, or one-to-many? Notes from Chris Episode 2994 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 freelance nutritionist who transitions from perso…
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In this week’s Throwback Thursday segment, learn how one test prep tutor goes from juggling individual clients to running a membership platform filled with guided lessons, practice tests, and group support. 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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#block-7744ebfa h2 { width: 401px; } What It’s About YouTube was this Mexican’s artist pathway to fame. Notes from Chris Episode 2993 In today’s story… A lesson in persistence and tweaking. So important! It’s also an artist success story… a major one. Specially, it’s about a Mexican artist who was a struggling painter and sculptor, but then becomes…
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A struggling painter and sculptor uploads a drawing video to YouTube and discovers a massive audience for tutorials on hand-drawing, generating over 50 million views in 6 years. 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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In this episode, we help an aspiring event planner manage indecisive clients who keep changing their event themes. Learn how to set clear expectations, avoid delays, and charge for extra work—without coming across as pushy. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without qu…
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In this week’s First $1,000 segment, find out how one Bay Area event planner turns suitors’ dreams into carefully choreographed reality, complete with hidden photographers and heartfelt surprises. 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…
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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: assemble the nuts and bolts. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra mo…
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In this episode, we help a content creator navigate what to do when a brand uses their photo without permission. Learn how to approach the situation professionally—or when it might be better to let it go and move forward. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quit…
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In this episode, we help a freelance marketing consultant explore ways to turn her expertise into passive income. Learn how to create scalable products that generate revenue—even when you’re not working one-on-one with clients. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money withou…
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In this week’s Throwback Thursday segment, discover how a freelance nutritionist transitioned from personal meal plans to comprehensive corporate wellness programs, creating ongoing value for employees and stable income for herself. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money w…
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Three friends embrace the reality of pubic area discomfort and build a pubic oil businesses from scratch, turning it into a six-figure side hustle despite the skepticism of literally every person they talked to. 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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In this episode, we help a small business owner decide whether to relaunch a product that didn’t perform well the first time. How can she turn a past flop into a future success? 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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In this week’s First $1,000 segment, discover how one retiree used his CDL experience to deliver RVs cross-country, getting paid while exploring the open 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 lesso…
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