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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.
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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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#block-aee1732c h2 { width: 401px; } What It’s About If you could turn back time—would you want to? Notes from Chris Episode 2887 In today’s episode, we’re diving into a big question: Is it easier or harder to start and profit from an online project compared to seven years ago? The internet has changed a lot in the past decade—there are more tools,…
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In today’s episode, we explore whether it’s easier or harder to start an online business today compared to seven years ago. Find out how the landscape has changed and what it takes to stand out in a crowded market. 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-e2200dae h2 { width: 401px; } What It’s About Cruise lines often feature “digital art” on monitors. Notes from Chris Episode 2886 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 $100,00…
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In this week’s “First $1K” segment, we hear from a digital artist who licensed their artwork to cruise lines for use on TVs and digital displays. Discover how this unique niche led to earning the artist her first $1,000. 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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#block-a04853de h2 { width: 401px; } What It’s About If something has no physical presence, how can you increase its value? Notes from Chris Episode 2885 Today’s question comes from Wesley in Madison, Wisconsin. He’s selling digital products and wants to know how to make them feel more valuable and appealing to his customers. Digital products can b…
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In today’s episode, we discuss how to package and present digital products in a way that increases their perceived value. 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 …
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#block-f3a95b88 h2 { width: 401px; } What It’s About What’s the best way to use Reels? Notes from Chris Episode 2884 In today’s episode, we’ve got a great question from Clara in Austin, Texas. She’s looking to use Instagram Reels to promote her side hustle but isn’t quite sure how to make the most of this feature. If you’ve been wondering how to ta…
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On today’s episode, we’re breaking down how to use Instagram Reels to grow your side hustle. From product showcases to behind-the-scenes content, find out how you can create engaging Reels that capture attention and drive sales. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money witho…
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#block-8ffa3630 h2 { width: 401px; } What It’s About A cease-and-desist request has the intended effect. Notes from Chris Episode 2883 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 mist…
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In this week’s Failure Friday segment, we follow a small business owner whose clever branding leads to an unexpected legal battle. 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 d…
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#block-0ef8baa9 h2 { width: 401px; } What It’s About It’s … a lot of algae in one place! Notes from Chris Episode 2882 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 the owner of a pop-up stationery business t…
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In this week’s “Throwback Thursday” segment, we catch up with the owner of a small-scale algae farm in Wisconsin who’s ridden the wave of plant-based supplement popularity. 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…
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#block-0091fc01 h2 { width: 401px; } What It’s About Social proof is important—how can you get it? Notes from Chris Episode 2881 Today’s question comes from Elena in Oceanside, California. She’s been running her side hustle for a few months and wants to gather customer testimonials to build trust and credibility, but isn’t sure how to go about it.I…
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In this episode, we explore the best ways to gather customer testimonials for your side hustle. This is important! 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. S…
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#block-cac1add4 h2 { width: 401px; } What It’s About How can you do everything?? Notes from Chris Episode 2880 Today’s question comes from Naomi in Chicago. She’s juggling a 9-to-5 job while trying to grow her side hustle and wants to know the best way to structure her day for maximum productivity without burning out. If you’re trying to find that …
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In this episode, we explore how to balance a full-time job with a side hustle. The struggle is real! 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: Sid…
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#block-5c952259 h2 { width: 401px; } What It’s About A smart idea to bring families together around the jigsaw table. Notes from Chris Episode 2879 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 fi…
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In this week’s “First $1K” segment, we hear from a side hustler who starts a custom jigsaw puzzle business, turning personal photos into unique puzzles sold on Etsy. 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 episode, we dive into how to use LinkedIn to find your first freelance client. Discover simple strategies to optimize your profile, connect with the right people, and stand out in a crowded market. 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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In this episode, we discuss how to leverage your side hustlin’ experience to negotiate a raise or promotion at your day job. 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 ea…
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In this week’s Failure Friday segment, we meet a freelance writer whose eagerness to boost her side income leads to a scheduling nightmare. Organization is everything! 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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In this week’s “Throwback Thursday” segment, we hear from the owner of a pop-up stationery business that’s evolved from occasional events to a thriving part-time enterprise. 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 fre…
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In this episode, we explore strategies for introverts to market their side hustles without feeling overwhelmed. Such a thing is 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 lessons and listener Q&A se…
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In this episode, we explore how to start an ASMR content creation side hustle. (And if you don’t know what ASMR is, you’ll learn that too!) 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 …
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In this week’s “First $1K” segment, we hear from a nurse who turned her expertise in health and safety into a side gig as a disaster preparedness consultant, helping individuals and businesses prep for emergencies. 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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In this episode, we explore ways to use storytelling to market your side hustle or small business, and make it stand out 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 sev…
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In this episode, we reveal the magic number of copies you need to sell in one week to make the New York Times bestseller list. A caller from last month returns with an important follow-up! 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 sh…
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In this week’s Failure Friday segment, we follow a fitness coach's journey into the world of virtual workouts, where their DIY approach to social media marketing leads to disappointment. 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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In this week’s “Throwback Thursday” segment, we hear from an electrical engineer who turned his technical expertise into a thriving side gig installing smart home systems. 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 …
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In this episode, we discuss strategies for setting boundaries with clients when your side hustle isn’t your main job. Learn how to communicate effectively, manage expectations, and maintain a healthy balance between your side hustle and full-time job. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who…
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