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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-eb7070dc h2 { width: 401px; } What It’s About Are you paying too much money every month? Chances are, the answer is yes! Notes from Chris Episode 2912 Welcome back to Side Hustle School. Today’s question comes from Ryan in New Orleans, who recently found out he’s been paying for a bookkeeping subscription for three years without actually usi…
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In today’s episode, we help a listener figure out what to do after paying for multiple subscriptions they haven’t used: a common and unfortunate problem. 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…
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#block-735142fe h2 { width: 401px; } What It’s About Burnout is real, especially with client work that can’t easily be rescheduled. Notes from Chris Episode 2911 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 s…
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In this week’s “Failure Friday” segment, we hear from a tech professional who started offering design and development services as a side hustle. As the business grew, balancing it with a full-time job and personal life becomes overwhelming, leading to stress and performance issues at work. Side Hustle School features a new episode EVERY DAY, featur…
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#block-8f025621 h2 { width: 401px; } What It’s About There’s an unending market for planners! Notes from Chris Episode 2910 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. Today, in our latest feature, we’ll hear from a side hustler wh…
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In this week’s “Throwback Thursday” segment, we hear from a side hustler whose passion for organization and design morphed into a steady income stream while maintaining her 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 incl…
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#block-691d35f6 h2 { width: 401px; } What It’s About If customers spend more, you’ll earn more—even without adding new customers. Notes from Chris Episode 2909 Today we have a question from Angela in Phoenix, who’s been running a successful online store for about a year. She’s looking to increase her average order value and wants to know the best w…
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In today’s episode, we help a listener with strategies to boost the average order value of her online store. We’ll cover upselling, cross-selling, and other techniques to increase sales in a way that feels natural and customer-friendly. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra mon…
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#block-f615dcf7 h2 { width: 401px; } What It’s About The Kardashians are too expensive, but what about all of these smaller celebs?? Notes from Chris Episode 2908 Today’s question comes from Sam in Nebraska, who’s building an e-commerce brand and thinking about how to market it effectively. He’s considering investing in a micro-influencer campaign …
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In today’s episode, we help a listener decide whether to use micro-influencers to promote their e-commerce brand. Should they hire through an agency or go the DIY route to save money? 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 in…
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#block-80ad1484 h2 { width: 401px; } What It’s About She doesn’t own property in the Netherlands—she just looks after it (and gets paid for the work). Notes from Chris Episode 2907 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 the…
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In this week’s “First $1K” segment, we hear from a Dutch side hustler who turned her organizational skills into a profitable business by managing Airbnb properties for homeowners. 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 includ…
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#block-90ca2344 h2 { width: 401px; } What It’s About What’s the best way to reach out via cold email? Notes from Chris Episode 2906 Today’s question comes from Jay in Brooklyn, who’s working on a side hustle selling client services. He’s reaching out to potential clients through cold emails but feels like his messages are falling flat. He’s looking…
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In today’s episode, we help a listener refine their cold email strategy to get more client responses. Learn how to craft personalized, value-driven messages that convert, without sounding like a template. 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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#block-7b13b221 h2 { width: 401px; } What It’s About How should you sell tickets—in phases, or all at once? Notes from Chris Episode 2905 Welcome to another episode of Side Hustle School. Today, we’re hearing from Laura in San Diego, who’s planning to sell tickets for an event she’s hosting. She’s wondering whether it’s better to release tickets on…
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Today’s episode tackles a question about the best way to sell tickets for an event. Should you keep sales open on a rolling basis or create urgency with a waitlist and limited sale dates? 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 sho…
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#block-88688dd1 h2 { width: 401px; } What It’s About Turns out private property is a real thing. Notes from Chris Episode 2904 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, mi…
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In this week’s “Failure Friday” segment, we hear from the owner of a mobile massage service who set up shop in front of a busy mall, only to get shut down by mall management. Oops! 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-a3d65cc0 h2 { width: 401px; } What It’s About Ho ho ho! Lots of letters are going out in the mail—still. Notes from Chris Episode 2903 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 whose…
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In this week’s “Throwback Thursday” segment, we hear from the “Letters from Santa" operator whose side hustle has experienced significant growth in the past two years. She now earns more than $25,000 each holiday period. 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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In today’s episode, we help a listener who’s brand new to the digital space figure out where to start with their side hustle. We’ll cover the first steps for getting online, building an audience, and setting yourself up for long-term success. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ext…
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Today’s episode tackles a question from a listener wondering whether to start a new side hustle or focus on scaling their current one. We explore both approaches and provide tips to help you choose the best path forward. 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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In this week’s First $1,000 segment, we hear from a DIY enthusiast who turned his knack for TV wall mounting into a profitable side hustle—without actually mounting any TVs himself. 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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In today’s episode, we explore the opportunities for non-adult content on OnlyFans. From fitness coaching to creative arts, discover how you can build a loyal audience—while remaining fully clothed! 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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In today’s episode, we discuss the hardest side hustles to start and manage. From fashion businesses dealing with inventory headaches to restaurants with high overhead costs, learn which side hustles come with the most challenges. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money wit…
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In this week’s “Failure Friday” segment, we hear from a content creator who launches a YouTube and TikTok channel focused on sharing uplifting political stories, inspired by popular "good news" channels. Unfortunately, finding enough positive political stories proves harder than expected! Side Hustle School features a new episode EVERY DAY, featuri…
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In this week’s “Throwback Thursday” segment, we hear from a side hustler whose passion for fitness transformed into a successful affiliate marketing blog. 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 an…
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Today’s episode tackles a question about recording videos for multiple platforms. Should you shoot in portrait or landscape mode? And is there a way to record once and use the content everywhere? We’ve got answers and tips to streamline your video production. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of pe…
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In today’s episode, we help a creator who’s building a solo travel platform decide whether to focus on one content platform or expand to multiple channels like Substack, TikTok, and podcasts. 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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In this week’s First $1,000 segment, we hear from the owner of a California signature-gathering business, which collects signatures for ballot initiatives. He earns more than $1 on every signature—and this money adds up! 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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