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


    • Oct 10, 2025 LATEST EPISODE
    • daily NEW EPISODES
    • 8m AVG DURATION
    • 3,260 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. 3205 - Q&A: “How do I license calming coloring pages to wellness apps?”

    Play Episode Listen Later Oct 10, 2025 4:48


    Trade $2 one-time sales for four-figure B2B deals. We build the pitch, pricing, and contract essentials for licensing art to wellness platforms. 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. 3204 - TBT: The Secret Author Behind Your Favorite Romance Novel

    Play Episode Listen Later Oct 9, 2025 5:20


    In this week’s Throwback Thursday segment, hear how one fanfiction writer went pro—now earning five figures per project ghostwriting for bestselling romance authors who don’t want their names published. 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. 3203 - STORY: Underwear Side Hustle Turns Into $500,000/Month Business

    Play Episode Listen Later Oct 8, 2025 7:00


    Two women launch an underwear brand in their spare time. It grows from an early Kickstarter campaign to a multi-million dollar company with more than a dozen employees. 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. 3202 - Q&A: “Can a ‘tech deals' newsletter really make money?”

    Play Episode Listen Later Oct 7, 2025 3:49


    Tech discounts can pay the bills, at least if you treat them like a product, not a hobby. Today we map out list-building, trust, and revenue math for a profitable deal newsletter. 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. 3201 - First $1,000: Weekend ASL Crash Courses for Hospitality Staff

    Play Episode Listen Later Oct 6, 2025 4:59


    In this week’s First $1,000 segment, hear how a certified interpreter turned empty hotel conference rooms into a training ground for quick, practical American Sign Language (ASL). 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. 3200 - Weekend Workshop: From Utah Piano Teacher to Digital Nomad

    Play Episode Listen Later Oct 5, 2025 5:57


    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: a $360,000/year online music school. 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. 3199 - Q&A: “How do I handle a non-compete that hurts my side hustle?”

    Play Episode Listen Later Oct 4, 2025 5:09


    A promotion with strings attached can stall a thriving side hustle. Today we’ll walk through reading the fine print, negotiating carve-outs, and keeping both your boss and your business on the road. 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. 3198 - Q&A: “I went viral, but now I can't meet demand!”

    Play Episode Listen Later Oct 3, 2025 5:23


    A viral spike is great—until it breaks your capacity. Today we map a four-step triage plan to pause the chaos, satisfy customers, and turn overwhelm into long-term buzz. 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. 3197 - TBT: Turning Property Management Experience Into Digital Products

    Play Episode Listen Later Oct 2, 2025 5:32


    In this week’s Throwback Thursday segment, learn how one former apartment manager turned their real estate experience into a template shop for landlords, helping them boost revenue without buying new properties. 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. 3196 - STORY: Google Employee Makes $100,000 Using Fiverr

    Play Episode Listen Later Oct 1, 2025 7:32


    In just one year, this Google product manager earned an extra $100,000 by providing marketing services on Fiverr.com. Learn his tips to hack the platform for yourself! 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. 3195 - Q&A: “Which passive-income model fits a consultant best?”

    Play Episode Listen Later Sep 30, 2025 6:13


    Want to escape the billable-hour treadmill? Today we map out three proven paths—courses, content, and compounding cashflows—that turn one-time effort into long-term 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. 3194 - First $1,000: Marketer Sells Simple Fixes to Dental Clinics

    Play Episode Listen Later Sep 29, 2025 5:11


    In this week’s First $1,000 segment, hear how a digital marketer gets paid for cleaning up Google listings for orthodontists—fixing visibility problems most offices didn’t even realize they had. 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. 3193 - Weekend Workshop: The Art of Electronics Arbitrage

    Play Episode Listen Later Sep 28, 2025 8:01


    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: buy low, sell high, repeat! 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. 3192 - Q&A: “How can a freelancer pay herself a stable salary?”

    Play Episode Listen Later Sep 27, 2025 5:39


    Feast-or-famine income doesn’t have to mean feast-or-famine life. Today we build a simple three-bucket system that turns lumpy freelance revenue into a steady, predictable paycheck. 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. 3191 - Q&A: “What KPIs should I track for my software biz?”

    Play Episode Listen Later Sep 26, 2025 4:23


    Fifty customers, fifty metrics—too many for a two-person team. Today we boil micro-SaaS analytics down to the three numbers that actually move 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.

    Ep. 3190 - TBT: Helping Aspiring Film Professionals Get Hired

    Play Episode Listen Later Sep 25, 2025 4:47


    In this week’s Throwback Thursday segment, learn how a London-based side hustler launched a service to help aspiring film crew members get their first jobs and union credentials—and how they’re now planning to expand to Los Angeles and Vancouver. 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. 3189 - STORY: College Grad Shares “More than Mac & Cheese” Student Recipes

    Play Episode Listen Later Sep 24, 2025 6:45


    When a college student learns to cook, she documents her recipes online, earning more than $1,000/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. 3188 - Q&A: “Can you run a YouTube channel with only AI voices and scripts?”

    Play Episode Listen Later Sep 23, 2025 4:15


    Can a faceless, AI-voiced show win viewers and ad dollars? Today we break down platform rules, audience psychology, and the tiny legal print you can’t ignore when the “host” is synthetic. 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. 3187 - First $1,000: Typography Lover Turns Letters Into Revenue

    Play Episode Listen Later Sep 22, 2025 5:19


    In this week’s First $1,000 segment, learn how a font designer earned their first digital payday with a clean, subway-inspired typeface. With just two fonts and a Creative Market listing, they passed $1,000 in less than a 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. 3186 - Weekend Workshop: Design Disruption in Traditional Markets

    Play Episode Listen Later Sep 21, 2025 5:47


    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: an astrology calendar for modern times. 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. 3185 - Q&A: “How can I sell an Amazon-only FBA brand for top dollar?”

    Play Episode Listen Later Sep 20, 2025 5:05


    Trying to sell an Amazon-only FBA brand? In this episode we talk valuation, “channel risk,” and a 90-day tune-up that can add tens of thousands to the sale price of a 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. 3184 - Q&A: “How can a coast-to-coast road trip pay for itself?”

    Play Episode Listen Later Sep 19, 2025 4:54


    A coast-to-coast road trip sounds expensive—unless you turn the highway into a revenue stream. Today we map out five travel-friendly hustles that can cover gas, motels, and maybe even a little profit. 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. 3183 - TBT: Creator Builds Instagram Mastermind Pod

    Play Episode Listen Later Sep 18, 2025 5:02


    In this week’s Throwback Thursday segment, hear how a social media strategist launched a private mastermind pod to help creators boost their Instagram engagement—sharing likes, comments, and algorithm tips. 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. 3182 - STORY: Personal Trainer Pumps Up Breakfast

    Play Episode Listen Later Sep 17, 2025 7:36


    A full-time personal trainer takes ‘breakfast of champions’ to the next level with pancakes that put the ‘pro’ in protein, earning $25,000/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. 3181 - Q&A: “Should my first info product be $30 or $300?”

    Play Episode Listen Later Sep 16, 2025 5:42


    Should you launch your first info product at a budget price or aim for a premium market? Today we unpack perceived value, buyer psychology, and the hidden costs of “cheap” customers—so you can price with confidence. 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. 3180 - First $1,000: Foot Traffic Nerd Turns Public Data Into Paid Service

    Play Episode Listen Later Sep 15, 2025 5:29


    In this week’s First $1,000 segment, hear how a data enthusiast built foot traffic reports for small landlords and local businesses, using public tools and smart packaging. 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. 3179 - Weekend Workshop: Building Systems That Sell Themselves

    Play Episode Listen Later Sep 14, 2025 6:52


    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 “guest post tracker” that earned recurring revenue. 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. 3178 - Q&A: “How do I stop every freelance project from starting in chaos?”

    Play Episode Listen Later Sep 13, 2025 5:24


    Do you begin every freelance project in panic-mode? In today’s episode we build a repeatable onboarding sequence that turns new clients into smooth projects—no assistant required. 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. 3177 - Q&A: “How can I make money by renting out houseplants?”

    Play Episode Listen Later Sep 12, 2025 4:11


    Can your living-room jungle become a revenue stream? In today’s episode, we explore the growing demand for short-term plant rentals and break down the numbers, logistics, and risks of turning leafy assets into cash. 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. 3176 - TBT: Helping High School Dropouts Start Plumbing Careers

    Play Episode Listen Later Sep 11, 2025 5:40


    In this week’s Throwback Thursday segment, learn how one side hustler partnered with trade schools to help high school dropouts gain life skills and secure paid apprenticeships in the plumbing trade. 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. 3175 - STORY: Movie Industry Friends Rewrite the Credits, Earn $20,000/Month

    Play Episode Listen Later Sep 10, 2025 6:40


    Those long credit sequences at the ends of movies can include a LOT of names—and they also take a lot of time for producers to coordinate. When two industry friends team up to simplify the process, they crawl their way to a highly profitable 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. 3174 - Q&A: “How can a first-time author stand out in a market of 4,500 books per day?”

    Play Episode Listen Later Sep 9, 2025 5:25


    With an estimated 4,500–6,000 English-language titles published each day, how can a first-time author avoid getting buried? Today we look at the real numbers—and a proven game plan for standing out. 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. 3173 - First $1,000: Houston Homeowner Turns Studio Into Weekend Venue

    Play Episode Listen Later Sep 8, 2025 6:28


    In this week’s First $1,000 segment, discover how one Houston homeowner transformed a simple backyard shed into a rentable studio for photos, workshops, and quiet retreats. 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. 3172 - Weekend Workshop: The Seasonal Business Goldmine

    Play Episode Listen Later Sep 7, 2025 7:11


    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 six-figure, six-week 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. 3171 - Q&A: “Managing cash flow across PayPal, Stripe, Venmo, and Etsy…”

    Play Episode Listen Later Sep 6, 2025 5:11


    Multiple payment platforms can feel like financial whack-a-mole. Today we lay out a four-step system to keep cash flow clear and tax time painless. 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. 3170 - Q&A: “Do followers still matter in the age of algorithms?”

    Play Episode Listen Later Sep 5, 2025 6:05


    If algorithms decide who sees your content, do follower counts still matter? Today we dig into how “algorithmic feeds” really work and why a loyal subscriber base still gives side hustlers a competitive edge. 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. 3169 - TBT: Selling Ads for Medical Conferences on Commission

    Play Episode Listen Later Sep 4, 2025 5:25


    In this week’s Throwback Thursday segment, hear how a freelance marketer started selling ad placements and sponsorships for medical conferences—on commission only—and turned it into a surprisingly consistent 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. 3168 - STORY: IT Guy Earns Extra $50,000/Year Restoring Vintage Radios

    Play Episode Listen Later Sep 3, 2025 7:09


    He wanted to start a side business and put his engineering degree to good use. When he stumbled across two 1950s radios, he found an idea that was right on his wavelength. 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. 3167 - Q&A: “How to handle customer service without burning out?”

    Play Episode Listen Later Sep 2, 2025 5:48


    Customer emails piling up? Today we show solo founders how to automate 60% of support, triage the rest, and reclaim their weekends—all while keeping buyers happy. 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. 3166 - First $1,000: Language Nerd Builds “Fake Language” Creation Kit

    Play Episode Listen Later Sep 1, 2025 5:58


    In this week’s First $1,000 segment, discover how a linguistics grad turned their love of invented languages into a digital toolkit for writers and gamers. With a simple Gumroad listing and a few community posts, they reached $1,000 in five weeks. 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. 3165 - Weekend Workshop: How Makeup Videos Built a Million-Dollar Brand

    Play Episode Listen Later Aug 31, 2025 7:46


    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: behind the scenes of an online makeup empire. 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. 3164 - Q&A: “Is there a market for fancy cookware rentals?”

    Play Episode Listen Later Aug 30, 2025 5:14


    Can you make money renting out fancy kitchen gear? In today’s episode, we explore whether luxury cookware rentals could work—and what hidden challenges you need to watch out 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, 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. 3163 - Q&A: “Can MacBook arbitrage work as a side hustle?”

    Play Episode Listen Later Aug 29, 2025 5:33


    Can you make money buying Apple computers in one country and reselling them in another? In this episode, we explore the appeal—and the reality—of international tech arbitrage. 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. 3162 - TBT: Failed App Becomes Successful Consulting Business

    Play Episode Listen Later Aug 28, 2025 5:06


    In this week’s Throwback Thursday segment, hear how one side hustler launched an app that didn’t take off, but ended up turning that hard-won experience into a consulting service for other early-stage founders. 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. 3161 - STORY: Curated Gift Boxes for Breakups and Baby Bumps

    Play Episode Listen Later Aug 27, 2025 6:56


    A breakup brings two sisters together to create one happy 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. 3160 - Q&A: “Can Lyft drivers really make $2,000/week?”

    Play Episode Listen Later Aug 26, 2025 4:36


    Can a Lyft driver really make $2,000 a week? In this episode, we break down rideshare earnings, what’s possible, and what’s rare. 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.

    BONUS: "Time Anxiety" Book and Free Quiz

    Play Episode Listen Later Aug 25, 2025 2:08


    A short update on my new book, Time Anxiety, including a free quiz you can take and a discount on the ebook version for U.S. listeners. 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. 3159 - First $1,000: YouTube Bonsai Channel Grows Into Online Store

    Play Episode Listen Later Aug 25, 2025 5:56


    In this week’s First $1,000 segment, hear how a niche YouTube creator turned their passion videos into a Shopify store—selling products directly to their growing 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. 3158 - Weekend Workshop: Template Biz Goes from Service to Scale

    Play Episode Listen Later Aug 24, 2025 7:01


    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: how a budget résumé design service morphs into a template business that generates passive 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. 3157 - Q&A: “How can I make money from old YouTube videos?”

    Play Episode Listen Later Aug 23, 2025 4:24


    Do you have any old videos that aren’t getting views? In this episode, we look at creative ways to repackage, remix, and monetize your past content for new platforms or audiences. 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. 3156 - Q&A: “Can you profit by reselling loyalty points or rewards?”

    Play Episode Listen Later Aug 22, 2025 4:57


    Can you really make money reselling loyalty rewards or points? In this episode, we break down the reality behind this internet hustle—and whether it’s worth your time. 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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