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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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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: learning to spot profitable ideas. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ex…
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#block-1761a6ed h2 { width: 401px; } What It’s About Are there good reasons for NOT having a solid guarantee with your offer? Notes from Chris Episode 2926 Today’s question comes from Marcus in Toronto, who runs a photography business and is considering offering a money-back guarantee on his services. He’s hoping it will build trust and attract mor…
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In today’s episode, we help a photographer decide whether to offer a money-back guarantee for his services. Learn how to build trust with clients while protecting your business from potential downsides. 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-68e89d4d h2 { width: 401px; } What It’s About Coaching can be a tough sell … unless you specialize. Notes from Chris Episode 2925 Today’s question comes from Darnell in Savannah, who recently started a leadership coaching business. He works with mid-level managers aiming for executive roles, but he’s concerned about standing out in a crowded…
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In today’s episode, we help a leadership coach stand out in an oversaturated market. Learn how to identify your unique value, niche down, and attract your ideal clients with strategies that work. 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-265e1032 h2 { width: 401px; } What It’s About Can you get cookies from a machine? In Oakland, you can—or at least you could for a while. Notes from Chris Episode 2924 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…
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In this week’s Throwback Thursday segment, we revisit two late-night bakers who created Oakland’s first cookie ATM. They share how this bold experiment evolved into a thriving pop-up and DIY cookie kit business. 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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#block-777119a8 h2 { width: 401px; } What It’s About Welcome to a brand new year! Notes from Chris Episode 2923 We’re back with an all-new season! Here’s how year nine (!) of Side Hustle School will work. Introducing new features, music, and another 365 days of episodes. SEE ALSO: Military Spouse Starts Subscription Box Mission:When an HR Director’…
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We’re back with an all-new season! Here’s how year nine (!) of Side Hustle School will work. Introducing new features, music, and another 365 days of episodes. 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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#block-afcfeb07 h2 { width: 401px; } What It’s About Pet adoption isn’t free—how can this pet lover support the practice sustainably? Notes from Chris Episode 2921 Welcome back to Side Hustle School. Today, we have a question from Lisa in Portland, who’s passionate about the ‘adopt, don’t shop’ movement and wants to turn that passion into a busines…
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In today’s New Year’s Eve episode, we help a listener explore how to turn their passion for the ‘adopt, don’t shop’ movement into a profitable 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 free guided lessons and …
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#block-213e7a85 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-b1989222 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-bd25ea61 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-cf0f46d6 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-810ebc31 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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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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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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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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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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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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