Side Hustle School

By Chris Guillebeau / Onward Project

Business Careers

What's Side Hustle School about?

A daily show for everyone who works a regular job and wants to start an income-earning project on the side. In each episode, listeners will hear a different story of someone who's started a side hustle—along with what went well, how that person overcame challenges, and what happened as a result. The show is written and hosted by Chris Guillebeau, the New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, and other books.

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LAST EPISODE

#2100 - Q&A: “I bought and...

10.01.2022

Today’s caller took advantage of the “pandemic Peloton” trend and resold dozens of them! He’s got a story for us, and he’s also wondering how to figure out what comes next. Side Hustle School features a new episode EVERY DAY, ...

Side Hustle School episodes:

10.01.2022 #2100 - Q&A: “I bought and sold 75 Peloton bikes…” Today’s caller took advantage of the “pandemic Peloton” trend and resold dozens of them! He’s got a story for us, and he’s also wondering how to figure out what comes next. Side Hustle School features a new episode EVERY DAY, ...
09.30.2022 #2099 - Failure Friday: “I had tears in my eyes reading the response…” In this week’s Failure Friday segment, we hear from a jewelry seller who almost gets taken out of commission by a highly negative review. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ...
09.29.2022 #2098 - TBT: “Thirty years a parking lot striper…” In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a longtime parking lot striper (not stripper!) who’s also written the definitive how-to guide on the topic. Side Hustle School features a new episode EVERY DAY, ...
09.28.2022 #2097 - Q&A: “I want to take my seminar on the road…” A listener has been teaching a local seminar on speed-reading. She now wants to take her show on the road … and quickly! What does she need to do next? Side Hustle School features a new episode EVERY DAY, featuring ...
09.27.2022 #2096 - Personal Finance Writer Monetizes Medium Posts Hoping to pay off his debt, a policy analyst begins writing about personal finance. Before long, he was earning more than $5,000/month. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra ...
09.26.2022 #2095 - First $1,000: “I left personal training to become a life coach…” In this week’s First $1,000 segment, we hear from a personal trainer who makes a big change to become a life coach. Is she able to manifest her way to a full slate of clients? Side Hustle School features a ...
09.25.2022 #2094 - Q&A: “I lost money on Bitcoin … is that tax-deductible?” If you began investing in cryptocurrency at the top of the market, you might be sitting on some pretty significant losses. Today’s caller is wondering if there’s a bright side: can these losses be deducted from your taxes? Side Hustle ...
09.24.2022 #2093 - Q&A: “I’m starting home improvement classes, with a twist…” A listener plans to offer a series of online home improvement classes. Is this a good idea—and if so, how can she connect with potential subscribers and paying customers? Side Hustle School features a new episode EVERY DAY, featuring detailed ...
09.23.2022 #2092 - Failure Friday: “I had to issue refunds and cancel 50 orders…” In this week’s Failure Friday segment, we hear from a successful Shopify store owner who sells party favors. Everything was going great, until disaster struck in the form of a misplaced change to her order panel. Side Hustle School features ...
09.22.2022 #2091 - TBT: Online Yoga for People with Chronic Illnesses In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Toronto yoga teacher who offers classes to people with chronic illnesses. She also works as a freelance writer and travels the world. Side Hustle School ...
09.21.2022 #2090 - Q&A: “How much income should I reinvest in my business?” It’s good to reinvest in your business, but not at any cost. Today’s caller wants to know if there’s a rule of thumb he can use in deciding where to put profits. Side Hustle School features a new episode EVERY ...
09.20.2022 #2089 - Six-Figure Lawn Business Becomes Sign of the Times A school teacher on maternity leave hits the books and finds her dream side hustle, replacing her day job income and then starting a second business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
09.19.2022 #2088 - First $1,000: “I sell t-shirts for pug lovers on Amazon…” In this week’s First $1,000 segment, we hear from an Amazon Merch on Demand seller. She’s sold thousands of t-shirts through the platform, and has a few tips on what works best. Among other things, shirts for dog lovers are ...
09.18.2022 #2087 - Q&A: “Is it more important to be knowledgeable or relatable?” A listener is trying to grow his Instagram following. Seems easy enough, right? Actually, no—lots of people struggle with this! It’s a crowded, competitive space. What is the crucial characteristic for success? Side Hustle School features a new episode EVERY ...
09.17.2022 #2086 - Q&A: “Can I get paid to teach people to play video games?” Today’s caller is skilled at gaming, but can he make money from it? He also has a caveat: no eSports. He doesn’t want to play games competitively, he wants to take his knowledge and earn from it. Side Hustle School ...
09.16.2022 #2085 - Failure Friday: "My boss discovered my side hustle by accident..." In this week’s Failure Friday segment, we hear from a company employee who starts a side hustle making websites during the workday. It goes well—until he steps away from his computer for lunch and forgets to change his desktop! Side ...
09.15.2022 #2084 - TBT: “I finally learned to let go and delegate…” In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of FranchiseFilming.com. Since his last feature, he’s increased his team and business 10x! Side Hustle School features a new episode EVERY DAY, featuring detailed ...
09.14.2022 #2083 - Q&A: “What kinds of guides or reports sell the best?” One of the ways you can profit from your knowledge is by compiling that knowledge into a detailed guide, report, or owner’s manual of sorts—then selling that material. Today’s caller has a smart question: what kinds of guides sell the ...
09.13.2022 #2082 - Nanotech Scientist Creates Antimicrobial Product After creating an antimicrobial coating for facemasks, a scientist applies the product to his own armpits in an attempt to reduce odor from his bike rides to and from the lab. Side Hustle School features a new episode EVERY DAY, ...
09.12.2022 #2081 - First $1,000: “I got paid to walk dogs while I was on work calls…” In this week’s First $1,000 segment, we hear from a Chicago native who starts “Day Job Dogwalking” during the pandemic. While juggling work calls with her employer, she gets paid (and eventually hires someone) to walk dogs in her neighborhood. ...
09.11.2022 #2080 - Q&A: "I made a bet to start a business in one day…" A listener made a bet with a friend that they can start a business and get at least one paying customer in a single day. Let’s take that bet and see if we can help! Side Hustle School features a ...
09.10.2022 #2079 - Q&A: “How does move-to-earn work—is this real?” A couple months ago I wrote about my experience with the Web3 app known as StepN, which pioneered the move-to-earn concept. It’s been an interesting journey, and today a listener calls in to request an update. Side Hustle School features ...
09.09.2022 #2078 - Failure Friday: “It should have been a small mistake…” In this week’s Failure Friday segment, we hear from the owner of an organic cosmetics brand. She was diligent with her product launches and had it down to a system–one that she may have trusted a bit too much. Side ...
09.08.2022 #2077 - TBT: “You Don’t Know My Life” Party Game Goes Global In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-creator of a boxed party game for adults called You Don’t Know My Life. During the pandemic, he started another side hustle hosting virtual game ...
09.07.2022 #2076 - Q&A: “One-page business plan: what is the essential info?” I once published a one-page business plan that a lot of people have used and referred to over the years. Today, our caller wonders: what is essential about this plan? Can you really explain an entire business in a few ...
09.06.2022 #2075 - Roadside Fruit Empire Produces Sweet Success A roadside peach stand pays for college tuition, turning into a bigger business along the way. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This ...
09.05.2022 #2074 - First $1,000: “You can’t sell anything until you list it…” In this week’s First $1,000 segment, we hear from the owner of an Etsy shop called The Blue Breakfront. After making a few rookie mistakes, she leveled-up and began getting steady sales. Side Hustle School features a new episode EVERY ...
09.04.2022 #2073 - Q&A: “How can I compete with unfair Etsy sellers?” We had an episode recently with an Amazon seller who had a competitor posting lots of fake reviews. Today’s caller has been dealing with a similar issue: unfair Etsy sellers who mass-manufacture their products, contrary to the platform’s seller policy. ...
09.03.2022 #2072 - Q&A: “How to best use a time of unemployment?” Today’s caller faces a big decision: during a time of unemployment, does she stretch her side hustle into a career, or go back to traditional work? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
09.02.2022 #2071 - Failure Friday: “I thought I’d set up the website incorrectly…” In this week’s Failure Friday segment, we hear from a middle-school principal from Pennsylvania. When he starts a blog for high-school volleyball players, it doesn’t get off to a smashing start. Side Hustle School features a new episode EVERY DAY, ...
09.01.2022 #2070 - TBT: Mochi-Making Classes Transition Online In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of KaorisKitchen.com. She started teaching mochi-making classes in the Bay Area, but pivoted to a new business selling mochi donuts locally. Side Hustle School ...
08.31.2022 #2069 - Q&A: “Too many coaches! I know I need to ‘choose a niche,’ but how?” Today’s listener is a life coach who’s heard me say that the way to succeed with this kind of personal service is to choose a focus or niche. Fair enough … but how do you do that? Side Hustle School ...
08.30.2022 #2068 - College Friends Start Utah Fulfillment Center Two friends learn the logistics of running a fulfilling business. In their first month of operation, they handled 3,000 orders for a Kickstarter project. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ...
08.29.2022 #2067 - First $1,000: Lutheran Pastor Sells & Ships “Consecrate” Boxes In this week’s First $1,000 segment, we hear from the creator of Consecrate, a subscription box for pastors and ministers. She sends more than 500 boxes out each month! Side Hustle School features a new episode EVERY DAY, featuring detailed ...
08.28.2022 #2066 - Q&A: “How do you forecast earnings for a side hustle?” A listener came across my back-of-the-napkin spreadsheet template and is wondering something: if a business or side hustle is new, how can you forecast earnings for it? It’s a good question, but there’s also a good answer. Side Hustle School ...
08.27.2022 #2065 - Q&A: "They asked for a refund after three hours of coaching..." After completing two long sessions with a client, a new coach received a request for a refund. Should she revise her policy of “money back with no questions asked”? Side Hustle School features a new episode EVERY DAY, featuring detailed ...
08.26.2022 #2064 - Failure Friday: “This is super embarrassing looking back…” In this week’s Failure Friday segment, we hear from an Atlanta designer. In addition to her full-time day job, she’s the owner of a stationary brand called Lucky Dog Design. Selling her products on Amazon seemed like a logical idea, ...
08.25.2022 #2063 - TBT: Baseball Training School Slides Into Growth In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of a baseball training academy. During the pandemic, he opened an additional business selling training gear on Amazon. Side Hustle School features a new ...
08.24.2022 #2062 - Q&A: “Can I sell the same thing with two business names?” Today’s caller is wondering if she can sell the same line of products with two different brand names. Is this clever or unethical? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ...
08.23.2022 #2061 - TV Producer Invents Sustainable Toothpaste Alternative After traveling non-stop for a busy job, a TV producer aims to reduce her plastic consumption. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This ...
08.22.2022 #2060 - First $1,000: “We began with a single sports team…” In this week’s First $1,000 segment, we hear from the founder of a sports leadership coaching business. He got his start by volunteering at a local school, and it quickly grew into something more. Side Hustle School features a new ...
08.21.2022 #2059 - Q&A: “Amazon Prime Day, but for side hustlers…” Today’s listener is wondering about a side hustle version of Prime Day. Can there be such a thing, or should the smaller sellers of the world simply piggyback on what Amazon has done since everyone is shopping anyway? Side Hustle ...
08.20.2022 #2058 - Q&A: “How do I transition from Etsy to Shopify?” A listener has been selling on Etsy and wants to make the switch to Shopify. What’s the best way to do this? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra ...
08.19.2022 #2057 - Failure Friday: “Then one afternoon I got a call from the police…” In this week’s Failure Friday segment, we hear from Dev Chakravarty from the U.K. He had an idea to start a rental car company for electric vehicles. This turned out to be much more difficult than he expected! Side Hustle ...
08.18.2022 #2056 - TBT: Philly French Toast Bites Take Over In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Lokal Artisan Foods, offering delicious french toast bites in Philadelphia and beyond. Side Hustle School features a new episode EVERY DAY, featuring detailed ...
08.17.2022 #2055 - Q&A: "I sold more by raising my prices—is that wrong??” Today’s listener has a moral dilemma: they made more money by raising their prices! Wait, what’s wrong with that? Listen to their question to find out. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
08.16.2022 #2054 - Health-Conscious Coffee Lover Steeps Into Crowded Market Taking a cue from her Carda-Mom, a sales professional creates steepable coffee flavoring bags containing organic spices instead of artificial syrups. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money ...
08.15.2022 #2053 - First $1,000: “It came from patience and vision boarding…” In this week’s First $1,000 segment, we hear from a wedding marketer who makes a vision board and sets out to build a new business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...
08.14.2022 #2052 - Q&A: “How to market audio services to Christian filmmakers?” Today’s caller seeks help marketing his services to a subset of faith-based filmmakers. Where can he find clients, and what does he offer them? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ...
08.13.2022 #2051 - Q&A: “How do creators get paid?” There are lots of ways an online creator can get paid. Which are the most common—and which are the most profitable? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money ...

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