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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 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promise of secure data wiping and refurbishment helped a tech-savvy neighbor earn thousands of dollars by flipping outdated electronics.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 …
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#block-641277cd h2 { width: 401px; } What It’s About Today’s episode comes from Day 18, which is all about the art of natural selling! Notes from Chris Episode 3039 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 man to gain the whole worl…
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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: the art of natural selling! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra mon…
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#block-2ccdb1c6 h2 { width: 401px; } What It’s About Side hustles keep getting cheaper… Notes from Chris Episode 3038 Starting a side hustle often means getting creative with limited resources—using what you have, borrowing what you don’t, and learning to do more with less. But as your hustle grows, the question of when to invest in tools or servic…
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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 l…
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#block-c4744fa8 h2 { width: 401px; } What It’s About Turn your weakness into a strength, right? Notes from Chris Episode 3037 Breaking into an industry where you don’t have formal training can feel intimidating, but sometimes, that fresh perspective is exactly what sets you apart. Today’s question comes from Beatrice in Berlin, who launched a colle…
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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 guid…
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#block-9a041364 h2 { width: 401px; } What It’s About Remote filming allows this traveling videographer to stay home. Notes from Chris Episode 3036 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 side hustler …
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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…
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#block-7386c17c h2 { width: 401px; } What It’s About Dogs love this canine-friendly ice cream. Notes from Chris Episode 3035 In today’s story… … frozen yogurt dog treats are on the menu today … the side hustle menu. Listen to today’s episode to learn more… SEE ALSO: Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain …
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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 da…
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#block-f125223e h2 { width: 401px; } What It’s About An interesting question! How can you show you care (as a brand) without virtue signaling? Notes from Chris Episode 3034 Incorporating values like sustainability or activism into a business can be powerful, but it also comes with the challenge of staying authentic. Today’s question comes from Elli…
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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 …
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#block-85b45f8b h2 { width: 401px; } What It’s About A Brooklynite feeds her neighborhood with local produce boxes. Notes from Chris Episode 3033 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, 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 …
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#block-b5dcaa16 h2 { width: 401px; } What It’s About Today’s episode comes from Day 17, which is all about which is all about publishing your offer. Notes from Chris Episode 3032 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 man to gain …
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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: publishing your offer! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money wi…
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#block-09b059d2 h2 { width: 401px; } What It’s About If you want to sell a course with a high ticket price, what do you need to know? Notes from Chris Episode 3031 Online courses have become one of the most popular ways for professionals to share their expertise, but standing out in a crowded market takes careful planning. Today’s question comes fr…
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In today’s episode, we explore how to create a standout premium online course. Learn how to structure it, position it for a high price point, and stand out in a competitive 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 inclu…
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#block-d51a4a7a h2 { width: 401px; } What It’s About A near Failure Friday story! But fortunately this side hustler manages to recover. Notes from Chris Episode 3030 Even the best-laid plans can be thrown off by an unexpected glitch, especially when running a side hustle. Today’s question comes from Neil in Brisbane, who experienced a payment syste…
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What happens when a tech glitch disrupts your side hustle? In this episode, we tackle how to prepare for unexpected challenges without overcomplicating your operations. 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 gui…
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In this week’s Throwback Thursday segment, discover how this side hustler built a spring break site that soars to $8,000 during peak months by combining ad networks with carefully edited AI 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 ye…
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When this student found himself in thousands of dollars worth of debt, he made a simple $40 investment that would go on to transform his life and reach tens of thousands of people around the world. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This yea…
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Why do a few things in your business drive most of your results? In this episode, we break down how power laws work and how to focus on what truly moves the needle. 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 …
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In this week’s First $1,000 segment, discover how one meticulous organizer built an online concierge service, offering tiered subscriptions for routine tasks and real-time support. 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 inclu…
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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: how to spend 10% more time on your most important tasks. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies…
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In this episode, we explore the ins and outs of running a tool rental business. Learn how to manage inventory, minimize risks, and maximize profits in this potentially lucrative 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 …
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AI tools like ChatGPT are exploding in popularity, but can creating templates for these tools become a profitable side hustle? In this episode, we explore the opportunities, challenges, and potential pitfalls of this idea. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without qui…
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In this week’s Throwback Thursday feature, discover how pivoting from digital art prints to creating mockups for Etsy and Shopify turned an underperforming side hustle into a high-demand service. 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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Two immigrants from Laos meet the needs of an underserved community, creating a series of dual-language flash cards and other resources. 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 sev…
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