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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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This week on Failure Friday, we tune into a venture of online guitar lessons. This post-pandemic digital adaptation missed its mark with beginners, and then faced a tough lesson on the irreplaceable value of in-person instruction. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money wit…
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#block-edba43d9 h2 { width: 401px; } What It’s About Student loans are big business these days. Notes from Chris Episode 2644 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 semi-retired inventor who’s now de…
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In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a student loan advisor who transformed a personal challenge into a thriving consultancy. 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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#block-82a61e56 h2 { width: 401px; } What It’s About What’s wrong with the “Follow my journey” approach? Notes from Chris Episode 2643 Alex from Dublin is asking a question a lot more bloggers should ask—and it’s not just bloggers, but that’s kind of where it started. “Follow my journey”—well yeah, but why? If I’m your grandma, I might be intereste…
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Discover how to turn your life story into an impactful product offering. Learn to craft courses, services, and community challenges that not only share “your journey” but also empower and transform others. 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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#block-0649d2b3 h2 { width: 401px; } What It’s About Is there an easy way to plan out your social posts? Notes from Chris Episode 2642 In the fast-paced world of fashion and the dynamic realm of side hustles, having a well-organized social media strategy is crucial. The key to managing this effectively is a robust social media calendar that keeps y…
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In today’s episode, we dive into the world of social media strategy for fashion brands and side hustles. Discover how to effectively organize and schedule your content across multiple platforms using a variety of tools, from Google Calendar and Trello to Hootsuite and Canva. Side Hustle School features a new episode EVERY DAY, featuring detailed ca…
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#block-21f612ba h2 { width: 401px; } What It’s About This video editor found a focus in Instagram Reels. Notes from Chris Episode 2641 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 $100,000—…
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In this week’s First $1,000 segment, we hear from a savvy video editor who turns Instagram Reels into a lucrative career, showcasing the art of engaging short-form 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 year, the show includes free…
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#block-dbc9ec5d h2 { width: 401px; } What It’s About What should be free and what should be “paid”? Notes from Chris Episode 2640 Nora from Boston is at a pivotal moment many content creators face: deciding how to monetize her blog on sustainable living without alienating her audience. The challenge lies in striking a delicate balance between free …
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In today's episode, we tackle the challenge of monetizing a blog through paywalled content. Learn how to balance free and paid content on your site, ensuring you continue to grow your audience while providing clear value to paying subscribers. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ex…
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#block-d6a3e4bb h2 { width: 401px; } What It’s About Did you know that TikTok takes a commission on earnings of up to 70%?! Notes from Chris Episode 2639 In today’s digital age, monetizing content on platforms like TikTok has opened up new avenues for creators. However, understanding the complexities of these platforms, especially when it comes to …
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In today's episode, we decode TikTok's Creator Fund commission structure and discuss strategies for maximizing earnings as a content creator. 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&…
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#block-901df81c h2 { width: 401px; } What It’s About Some coaches are worth hiring—just not this one! Notes from Chris Episode 2638 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 mistake…
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In this week’s Failure Friday segment, we hear about the unfortunate experience of hiring a business coach—a decision that led to costly lessons in a side hustler trusting her intuition and recognizing the value of her own business acumen. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra …
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#block-606c431b h2 { width: 401px; } What It’s About A therapist gets creative on serving clients outside her area. Notes from Chris Episode 2637 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 semi-retired i…
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In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a licensed therapist who diversifies her income by offering non-licensed coaching services to out-of-state clients. 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-e20d9bdb h2 { width: 401px; } What It’s About Should you post consistently, or just whenever feel “creative”? Notes from Chris Episode 2636 Welcome to a common crossroads in the world of content creation, where consistency meets creativity. Jamal, a freelance writer and blogger from London, brings us a question many creators ponder: the impo…
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Join us in today's episode as we delve into the art of maintaining a consistent yet flexible publishing schedule for bloggers. Learn how regular posting, tailored to your lifestyle and type of content, can improve engagement and growth. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra mon…
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#block-6ae10277 h2 { width: 401px; } What It’s About Can you use the project tool Notion to keep up with side hustles? Notes from Chris Episode 2635 In the bustling world of freelance web design, managing multiple projects efficiently is crucial for success and client satisfaction. Kevin from Toronto highlights a common challenge among freelancers:…
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In this episode, we dive into the world of digital organization tools for busy side hustlers. Discover how platforms like Notion can transform the way you plan, track, and collaborate on projects, ensuring nothing falls through the cracks. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra …
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In this week’s First $1,000 story, we dive into the innovative approach of a social media influencer who mastered the art of monetizing her fashion and home improvement Instagram accounts. 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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Discover how to tackle burnout head-on! This episode offers three key strategies for side hustlers to maintain their wellbeing without neglecting their passion for projects. 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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Today’s episode zeroes in the essential marketing strategies ideal for any side hustle. Discover how to effectively engage your audience, establish a strong online presence, and grow your customer base. 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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In this week’s Failure Friday segment, we bring you the story of "EduAI," an AI-driven tutoring platform whose technological complexity led to its downfall, underscoring the balance between innovation and usability in EdTech. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without …
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In this week’s “Throwback Thursday / Where are they now?” segment, we meet the semi-retired inventor who's now demystifying the patent process for new creators. 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 less…
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Join us in this episode as we help a listener find the magic number for her subscription box business. Learn how to calculate the number of subscriptions you need to be sustainable! 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 this episode, we discuss strategies for app developers to navigate Apple's 30% in-app purchase fee. Discover how alternative payment methods, subscription models, and cross-platform development can help maximize your app's revenue while staying within Apple's policy framework. Side Hustle School features a new episode EVERY DAY, featuring detail…
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In this week’s First $1,000 segment, we delve into the story of a college grad who creates a mentorship platform, connecting fraternity and sorority members with alumni for career guidance. 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 s…
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In this episode, we explore the pros and cons of live versus on-demand online courses, including some specific resources for course creation. Tune in to learn how to perfectly blend your teaching style with your audience's needs for the best learning experience. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of…
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