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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-23ef654c h2 { width: 401px; } What It’s About A smart project bringing in recurring income month after month. Notes from Chris Episode 2920 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 fir…
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In this week’s First $1,000 segment, we meet a web developer who turned his interest in ergonomic office furniture into a profitable side hustle. We explore how he built multiple niche websites that generated tens of thousands in commissions through Google AdSense. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies…
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#block-0671a33b h2 { width: 401px; } What It’s About If you can sell an online course … why would you give it away? Notes from Chris Episode 2920 Hey there! Today’s question comes from Tyler in Nashville, who’s wondering why I decided to give away an online course instead of selling it. We’ll talk through the strategy behind that decision, what I h…
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In today’s episode, we dive into the strategy behind giving away an online course for free. Was this a crazy idea, a strategic plan, or something else? 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 l…
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#block-141598db h2 { width: 401px; } What It’s About A new year is almost here! What should we expect? Notes from Chris Episode 2919 Welcome back to Side Hustle School. Today’s question comes from Megan in Boston, who’s wondering what 2025 might hold for side hustlers and small business owners. We’ll dive into some predictions about potential trend…
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In today’s episode, we dive into predictions for 2025—which is right around the corner! What trends, opportunities, and challenges should side hustlers and small business owners be preparing for? 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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#block-b1382979 h2 { width: 401px; } What It’s About It’s not always possible to replicate one platform’s results on another. Notes from Chris Episode 2918 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 s…
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In this week’s “Failure Friday” segment, we hear from a freelance graphic designer who found success on Upwork and decided to expand to Fiverr to grow her client base. However, the move to Fiverr led to a decline in client quality, causing issues with project expectations and delivery. Side Hustle School features a new episode EVERY DAY, featuring …
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#block-088ba73a h2 { width: 401px; } What It’s About Card commissions add up to serious cash for this side hustler. Notes from Chris Episode 2917 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 w…
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In this week’s “Throwback Thursday” segment, we hear from a fin-tech employee whose side project comparing credit cards grew into a profitable venture, earning $8,000/month in referral fees. 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-a79a76bb h2 { width: 401px; } What It’s About So far, so good—but what should this side hustle do next? Notes from Chris Episode 2916 Welcome back to Side Hustle School. Today’s question comes from Alex in Seattle, who’s already started a side hustle and has some early traction but isn’t sure what to focus on next. We’ll cover the top three …
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Merry Christmas! In today’s episode, we help a listener decide what to focus on next after gaining early traction with their 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 listener Q&A se…
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#block-44d33f18 h2 { width: 401px; } What It’s About Can you have an email address that more than one person checks? Notes from Chris Episode 2915 Welcome back to Side Hustle School. Today’s question comes from Sarah, who’s looking for a way to co-manage a business email account with her team. She’s wondering how to set it up so that multiple peopl…
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In today’s episode, we help a listener find the best way to co-manage a business email account with their team, including HelpScout, Hubspot, and more. 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 l…
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#block-dbb9a48d h2 { width: 401px; } What It’s About This sports fan found a way to get paid on sports fan betting. Notes from Chris Episode 2914 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 story, we follow a data analyst who turns his knack for numbers and love of sports into a profitable business. We explore how he developed fantasy sports prediction algorithms that helped him reach his first $1,000 in earnings. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra mone…
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#block-242d5f28 h2 { width: 401px; } What It’s About How do you know the value of a business for sale? Notes from Chris Episode 2913 Welcome back to Side Hustle School. Today’s question comes from Daniel in Atlanta, who’s considering buying a local business. He’s trying to understand how to calculate the return on investment (ROI) and what a reason…
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In today’s episode, we help a listener understand how to calculate ROI when considering buying a local business. We’ll cover how to estimate the payoff period, factors that impact profitability, and tools to make the analysis easier. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money …
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#block-94e79e27 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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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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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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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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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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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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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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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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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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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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