Side Hustle School

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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.

Chris Guillebeau / Onward Project


    • Jun 4, 2025 LATEST EPISODE
    • daily NEW EPISODES
    • 8m AVG DURATION
    • 3,131 EPISODES

    4.7 from 3,151 ratings Listeners of Side Hustle School that love the show mention: side hustles, chris g, extra income, listening to side hustle, extra money, start a side hustle, chris provides, quit your day job, money on the side, chris presents, chris offers, love chris's, side hustling, chris shares, chris has created, chris delivers, love the short format, get you thinking, liberia, i'm gaining.


    Ivy Insights

    The Side Hustle School podcast is a must-listen for anyone looking to start or grow their side hustle. From the very first episode, I was hooked on hearing about the creative and diverse range of side hustles featured on the show. It's inspiring to hear how each person has taken their unique passion and turned it into a profitable venture. Not only does this podcast offer realistic and insightful ideas, but it also provides actionable tips in a short amount of time, proving that building a successful side hustle is possible for anyone.

    One of the best aspects of this podcast is that it exposes listeners to a wide variety of ideas and concepts. While some may not resonate with everyone, it's valuable to learn about different approaches to side hustling and recognize what works best for you personally. Chris does an excellent job curating the businesses and products featured on the show, consistently finding unique and innovative ideas that spark creativity in listeners.

    Another great aspect of this podcast is Chris's ability to combine inspiration with actionability. His thoughts and ideas are not only motivational but also provide practical steps for implementing them in your own life. His insights have helped many listeners, myself included, turn their side hustles into successful ventures. The daily texts offering guidance on formulating ideas add an extra level of support and encouragement.

    There really isn't much negative to say about The Side Hustle School podcast. Occasionally, there may be episodes or stories that don't resonate as much with certain individuals based on personal interests or preferences. However, given the wide range of topics covered, there is always something new and interesting for everyone.

    In conclusion, The Side Hustle School podcast is an invaluable resource for anyone seeking inspiration, guidance, and motivation in pursuing their own side hustle. Chris's belief in "regular people" creating their own security and independence shines through in every episode. This podcast offers realistic advice, actionable ideas, and showcases numerous success stories from ordinary individuals who have turned their passions into profitable side hustles. Whether you're just starting out or already running a side business, this podcast will provide you with a wealth of knowledge and inspiration to help you grow and succeed.



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    Latest episodes from Side Hustle School

    Ep. 3077 - STORY: Four Friends Create Conversations, Earn $400,000 in 8 Months

    Play Episode Listen Later Jun 4, 2025 7:23


    Dark winter days were no match for four Dutch friends looking to spark meaningful conversations. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3076 - Q&A: “Should I add a live chat feature to my website?”

    Play Episode Listen Later Jun 3, 2025 4:45


    Does adding live chat to your website actually help sales, or does it just create more work? In this episode, we explore the pros and cons of live chat and whether it’s right for your 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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3075 - First $1,000: Marketing Pro Builds GPT Bots—No Code Needed

    Play Episode Listen Later Jun 2, 2025 5:52


    In this week’s First $1,000 segment, discover how one resourceful marketer built a thriving custom GPT chatbot service—despite having zero programming experience. Tune in to learn how they landed their earliest clients, structured their pricing, and scaled up without writing a single line of code. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3074 - Weekend Workshop: Measure What Matters

    Play Episode Listen Later Jun 1, 2025 8:17


    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: measuring what matters. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3073 - Q&A: “What's the purpose of more than one business bank account?”

    Play Episode Listen Later May 31, 2025 5:35


    Should you have more than one business bank account, or is that just extra complexity? In this episode, we break down why multiple accounts can help you manage cash flow, pay yourself better, and build long-term financial stability. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3072 - Q&A: “Why do struggling businesses keep their doors open?”

    Play Episode Listen Later May 30, 2025 4:35


    How do some retail stores stay open for years without making a profit? In this episode, we explore the hidden factors that keep struggling businesses afloat. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3071 - TBT: From DIY Pet Tributes to Six-Figure Etsy Shop

    Play Episode Listen Later May 29, 2025 5:47


    In this week’s Throwback Thursday segment, we hear from a maker who turned a small Etsy shop selling custom pet memorials into a thriving business. Since their last appearance, they’ve expanded their product line and found new ways to help grieving pet owners honor their companions. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3070 - STORY: High School Student Earns $20,000 Making Wooden Bow Ties

    Play Episode Listen Later May 28, 2025 6:42


    When a young woodworker receives a wooden bow tie as a gift, he’s unimpressed… so he learns to make his own and ends up earning $20,000 in a year as a high-school student. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3069 - Q&A: “I'm ready to sell my side hustle—how do I do it?”

    Play Episode Listen Later May 27, 2025 5:43


    How do you sell your side hustle without getting shortchanged? In this episode, we break down how to value your business, find the right buyer, and make a smooth exit. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3068 -First $1,000: Real Estate Office Rents Out Podcast Studio

    Play Episode Listen Later May 26, 2025 5:55


    In this week’s First $1,000 segment, discover how a small real estate office transformed an underused room into a podcast studio, bringing in steady income with minimal effort. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3067 - Weekend Workshop: Frame Your First Dollar

    Play Episode Listen Later May 25, 2025 6:19


    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: celebrating your milestones. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3066 - Q&A: “Is YouTube really ‘top of funnel' for educational creators?”

    Play Episode Listen Later May 24, 2025 5:21


    Is YouTube the best way to turn viewers into paying customers, or just a platform where people expect free content? In this episode, we break down whether YouTube really works as a sales funnel for 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 lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3065 - Q&A: “How do I take a break from my hustle without losing momentum?”

    Play Episode Listen Later May 23, 2025 5:36


    Can you take a break from your side hustle without losing momentum? In this episode, we explore how to pause your business the right way—and come back even stronger. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3064 - TBT: Turning Plastic into High-End Interior Pieces

    Play Episode Listen Later May 22, 2025 5:04


    This week’s Throwback Thursday feature highlights a 3D printing enthusiast who pivoted from small gifts to high-end home décor, creating unique pieces for upscale interiors. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3063 - STORY: Golfer Takes Swing At Content Website

    Play Episode Listen Later May 21, 2025 8:01


    A sales agency manager transforms his frustration with online golf advice into a thriving niche website generating $5,000 in monthly income. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3062 - Q&A: “Are there any ‘good' MLMs?”

    Play Episode Listen Later May 20, 2025 4:28


    Are there any ‘good’ MLMs, or are they all a bad idea? In this episode, we break down the truth about multi-level marketing and why it’s rarely a smart 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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3061 -First $1,000: Coffee Gear Affiliate Site Brews Profits

    Play Episode Listen Later May 19, 2025 7:14


    In this week’s First $1,000 story, learn how one coffee enthusiast brewed up an SEO-driven affiliate strategy, hitting $1,000 by offering thoughtful gear recommendations. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3060 - Weekend Workshop: Burn Down the Furniture Store

    Play Episode Listen Later May 18, 2025 6:46


    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: why you should ‘burn down the furniture store,’ AKA the power of special offers. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3059 - Q&A: “How can I wireframe a website?”

    Play Episode Listen Later May 17, 2025 4:48


    How do you wireframe a website without getting lost in the details? In this episode, we break down the best tools and strategies to map out your website idea before you build. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3058 - Q&A: “Is it a good time to launch a meme coin?”

    Play Episode Listen Later May 16, 2025 5:12


    Are crypto meme coins a viable side hustle, or are they just a fast track to failure? We break down the risks, rewards, and what it takes to launch a meme coin that actually lasts. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3057 -TBT: Crossing Borders, Boosting Orders

    Play Episode Listen Later May 15, 2025 7:01


    In this week’s “Throwback Thursday” segment, learn how a Canadian ecommerce expert turned his experience running an FBA shop into a consulting business, helping fellow Canadian sellers break into the lucrative U.S. market. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3056 - STORY: Architect Creates Mini-Blind Repair Too

    Play Episode Listen Later May 14, 2025 8:32


    It takes a long time to get to market, and success doesn’t come cheap—but this mini-blind “prescription” now earns an extra $15,000 a year for its inventor.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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3055 - Q&A: “Can you really publish a book in a week?”

    Play Episode Listen Later May 13, 2025 5:08


    Can you really write and publish a book in just one week? In this episode, we explore whether speed-publishing is realistic—or just a recipe for creating low-quality 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 guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3054 - First $1,000: Community Host Boosts Engagement and Retention

    Play Episode Listen Later May 12, 2025 5:49


    In this week’s First $1,000 story, learn how a personal touch and organized virtual events enabled one community manager to surpass the $1,000 mark while fostering a supportive space for solopreneurs. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3053 - Weekend Workshop: Test, Test, and Test Again

    Play Episode Listen Later May 11, 2025 6:51


    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: testing! 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3052 - Q&A: “How can I push past hesitation and market my creative work?”

    Play Episode Listen Later May 10, 2025 5:21


    In today’s episode, we help a listener overcome self-doubt and fear of judgment while launching a creative business. Learn how to build confidence and connect with the right audience. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3051 - Q&A: “How do I balance what I love with what the market wants?”

    Play Episode Listen Later May 9, 2025 4:21


    Is it better to focus on what sells or what you love making? In this episode, we explore how to balance passion and profit in a product-based 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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3050 - TBT: Lawn Sign Biz Expands to Wedding Décor Rentals

    Play Episode Listen Later May 8, 2025 5:28


    This week’s Throwback Thursday feature tells the story of a third-grade teacher who grew her creative lawn sign business into a go-to source for wedding décor. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3049 - STORY: Internet Trolls Eat Their Words In This Comedic Cake Hustle

    Play Episode Listen Later May 7, 2025 7:09


    After seeing a mean comment on Dolly Parton’s Facebook page, a woman realizes the absurdity of internet trolling and bakes up a hilarious and ironic 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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3048 - Q&A: “Best practices for Meta ads?”

    Play Episode Listen Later May 6, 2025 4:49


    Are Meta ads worth the investment? In this episode, we explore the best practices for running profitable campaigns on Facebook and Instagram in 2025. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3047 - First $1,000: Pop-Up Cosplay Salon Takes Con-Goers by Surprise

    Play Episode Listen Later May 5, 2025 6:36


    In this week’s First $1,000 story, discover how a Seattle hairstylist unofficially sets up shop near comic conventions—charging cosplayers for last-minute wig rescues and hair touch-ups. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3046 - Weekend Workshop: Ask 10 People for Help

    Play Episode Listen Later May 4, 2025 6:48


    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: building your support network. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3045 - Q&A: “Should I switch my business to a subscription model?”

    Play Episode Listen Later May 3, 2025 5:02


    Is switching to a subscription model the right move for your business? In this episode, we explore the pros, cons, and strategies for making the transition without alienating your 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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3044 - Q&A: “Why do authors offer pre-order bonuses?”

    Play Episode Listen Later May 2, 2025 5:30


    Why do so many authors offer pre-order bonuses? In this episode, we explore whether these perks drive sales or just create extra work—and how to decide if they’re right for your book launch. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3043 - TBT: From Cracked Screens to Tech Buyback Business

    Play Episode Listen Later May 1, 2025 5:34


    In this week’s “Throwback Thursday” segment, we hear from a college student who scaled from fixing cracked screens to creating a buyback platform that turns over $20,000 in inventory each month. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3042 - STORY: Fashion Buyer Creates Quirky Comfort Craze

    Play Episode Listen Later Apr 30, 2025 6:07


    Kyle Bergman has always had a unique and edgy taste in fashion. Then, thanks to one viral Buzzfeed article, he was able to create a brand that appeals to other people like him. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3041 - Q&A: “Should I expand the services I offer?”

    Play Episode Listen Later Apr 29, 2025 4:58


    How do you decide which new opportunities to pursue without overloading yourself? In this episode, we help a listener navigate expanding their business while staying focused and strategic. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3040 - First $1,000: Flipping Phones and Tablets for Fun and Profit

    Play Episode Listen Later Apr 28, 2025 5:36


    In this week’s First $1,000 segment, see how a simple promise of secure data wiping and refurbishment helped a tech-savvy neighbor earn thousands of dollars by flipping outdated electronics. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3039 - Weekend Workshop: Sell Like a Girl Scout

    Play Episode Listen Later Apr 27, 2025 5:48


    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: the art of natural selling! 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3038 - Q&A: “When is it worth spending money on your side hustle?”

    Play Episode Listen Later Apr 26, 2025 5:40


    When is it time to start spending real money on your side hustle? In this episode, we explore how to balance scrappiness with strategic investments to fuel growth. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3037 - Q&A: “How do I turn being an industry outsider into an advantage?”

    Play Episode Listen Later Apr 25, 2025 4:24


    How do you turn being an industry outsider into a strength? In this episode, we explore how to practice creativity while building trust and credibility 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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3036 - TBT: Montana Videographer Redefines Remote Filming

    Play Episode Listen Later Apr 24, 2025 6:26


    In this week’s Throwback Thursday segment, discover how a pro videographer ditched travel hassles by mailing filming kits worldwide and directing online course shoots entirely from afar. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3035 - STORY: Frozen Yogurt Dog Treats Are No Barking Matter

    Play Episode Listen Later Apr 23, 2025 6:04


    A Colorado couple creates a side hustle that gives dogs and their owners a way to enjoy their frozen treats from their own bowls. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3034 - Q&A: “How can I incorporate activism into my brand without seeming performative?”

    Play Episode Listen Later Apr 22, 2025 4:36


    How do you build a business that aligns with your values without coming across as performative? In this episode, we help a listener navigate authenticity in sustainability and activism. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3033 - First $1,000: Feeding the Neighborhood, One Block at a Time

    Play Episode Listen Later Apr 21, 2025 6:10


    In this week’s First $1,000 segment, learn how a backyard gardener in Brooklyn joined forces with neighbors to create hyper-local produce boxes, quickly earning $1,000 with minimal overhead. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3032 - Weekend Workshop: Launch Before You're Ready

    Play Episode Listen Later Apr 20, 2025 6:36


    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: publishing your offer! 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3031 - Q&A: “How do I create and sell a premium online course?”

    Play Episode Listen Later Apr 19, 2025 4:58


    In today’s episode, we explore how to create a standout premium online course. Learn how to structure it, position it for a high price point, and stand out in a competitive market. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3030 - Q&A: “How do I prepare for tech failures without overloading my setup?”

    Play Episode Listen Later Apr 18, 2025 5:36


    What happens when a tech glitch disrupts your side hustle? In this episode, we tackle how to prepare for unexpected challenges without overcomplicating your operations. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3029 - TBT: Travel Blog Becomes Spring Break Powerhouse

    Play Episode Listen Later Apr 17, 2025 6:22


    In this week’s Throwback Thursday segment, discover how this side hustler built a spring break site that soars to $8,000 during peak months by combining ad networks with carefully edited AI 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 guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3028 - STORY: College Student Hacks Into $40,000 A Month Side Hustle

    Play Episode Listen Later Apr 16, 2025 7:52


    When this student found himself in thousands of dollars worth of debt, he made a simple $40 investment that would go on to transform his life and reach tens of thousands of people around the world. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

    Ep. 3027 - Q&A: “How do side hustle ‘power laws' work?”

    Play Episode Listen Later Apr 15, 2025 5:45


    Why do a few things in your business drive most of your results? In this episode, we break down how power laws work and how to focus on what truly moves the needle. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes.

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