Q&A Episodes
Over 1,100 episodes of Side Hustle School are listener Q&As -- direct questions from people like you, answered by host Chris Guillebeau. These episodes cover every stage of the side hustle journey, from 'I have no idea where to start' to 'I'm ready to go full-time.' If you have a question, someone has probably already asked it -- and gotten an honest answer.
- Q&A: "I sold more by raising my prices — is that wrong??"
A listener raised her prices, then offered a coupon — and sales jumped. Is the "permanent sale" strategy wrong? Absolutely not. Side Hustle School Ep. 3493.
- Q&A: "How can I make a product to help with applied learning?"
A listener wants to help people learn how to learn — a valuable idea, but a tricky one to package. Here's how to approach it. Side Hustle School Ep. 3490.
- Q&A: "I'd like to sell an Apple Watch guide…"
A listener wants to sell a guide on getting the most from your Apple Watch — no manual is included. Here's how to price and promote it. Side Hustle School Ep....
- Q&A: "I'd like to sell a toolkit to sole proprietors…"
Jair from Portland wants to build a toolkit for sole proprietors — but "sole proprietors" is a very large market. Here's how to think about it. Side Hustle...
- Q&A: Are There Any Good MLM Companies?
A listener wants to know if any MLM companies are actually good. Chris has thoughts. (Spoiler: the business model is the problem.) Side Hustle School Ep. 3483.
- Q&A: "Recovering after a failed partnership…"
A listener's fashion partnership with a friend ended amicably — now she wants to try again solo but feels hesitant. Here's how to move forward with confidence....
- Q&A: "Is reselling gift cards a viable idea?"
A listener wants to go door-to-door buying unused gift cards and resell them. Is he missing something obvious? Probably not — here's how to think about it....
- Q&A: "How to identify target markets for livestreaming events?"
Leland wants to offer livestreaming content services to small businesses and events — but "small business" is a very wide net. Here's how to narrow it down....
- Q&A: "How to best use a time of unemployment?"
Today's caller is unemployed and weighing a big choice: grow the side hustle into a full-time career, or return to traditional work? Side Hustle School Ep....
- Q&A: "How should I promote my new app?"
Jiji from Orange County launched a paleo meal-planning app and wants to know how to get discovered in a crowded app store. Side Hustle School Ep. 3472.
- Q&A: "Where's the best place to hire contractors?"
Fiverr, Upwork, or OnlineJobs.PH — which is right for your side hustle? Plus tips for working with your first VA. Side Hustle School Ep. 3469.
- Q&A: "How do you determine a customer's emotional needs?"
Luke from Portland wants to know how to discover the core emotional needs behind any product or service — and what to do once you've found them. Side Hustle...
- Q&A: "Help! I'm stuck trying to find my 'ah-ha' idea"
Today's listener has inventoried her skills and kept her eyes open—but hasn't found her 'ah-ha' idea. Chris shares why you might not need one to get started....
- Q&A: "I stopped delivering for my Patreon…"
An independent musician has a Patreon account funded by loyal fans. He's stopped delivering for three months, but the fans keep paying. What should he do? Side...
- Q&A: "Should I pursue three ideas or just one?"
Today's caller has a dilemma: they have three independent ideas and aren't sure whether they should eliminate any of them. Side Hustle School Ep. 3461.
- Q&A: "How do you ethically source products made in overseas factories?"
There are lots of advantages to sourcing products from an overseas factory — but how do you know the working… Side Hustle School Ep. 3458.
- Q&A: "My 'road trip kit' for truck stops…"
A listener wants to sell a road trip kit — a compass, old-school atlas, air freshener, and novelty snacks — at truck… Side Hustle School Ep. 3455.
- Q&A: "Which is better: direct or indirect income?"
A listener has a clear business idea but isn't sure about the revenue model — get paid through affiliate and… Side Hustle School Ep. 3454.
- Q&A: "'Spaced repetition' practice with overseas tutors?"
Today's listener has an intriguing idea: to aid in memory retention using spaced repetition but with outsourced… Side Hustle School Ep. 3451.
- Q&A: "How to grow a YouTube channel with 121,000 subscribers?"
This Australian listener already has a very popular home cooking YouTube channel with more than 100,000 subscribers.… Side Hustle School Ep. 3448.
- Q&A: "How can I sell flash cards to pharmacy students?"
This listener has made a set of flash cards to help pharmacy students memorize generic drug names, but is having a… Side Hustle School Ep. 3447.
- Q&A: “How do I choose a revenue model for my coaching business?”
Most successful coaches have more than one source of income—but if you’re starting out and need to pick only one, which should you… Side Hustle School Ep. 3444.
- Q&A: “Can I file a small claims suit against a big business?”
Today’s caller is having a frustrating experience: they aren’t getting paid for work they’ve completed! Can they take their client… Side Hustle School Ep. 3441.
- Q&A: “What's the best platform for my idea?”
Do you start with your idea, or start with the ideal platform for your idea? Today’s caller wants to remain “platform agnostic.”… Side Hustle School Ep. 3440.
- Q&A: "How do I best prioritize next steps?"
How to prioritize your side hustle next steps when you have a product but aren't sure what marketing to tackle first. Side Hustle School Ep. 3437.
- Q&A: "Best way to get to market with nutrition bar…"
Launching a nutrition bar? Learn the steps to get your product on shelves, from taste to branding to distribution strategy. Side Hustle School Ep. 3434.
- Q&A: "Is the directory website model outdated?"
Directory websites for movers: outdated or valuable? How qualified traffic matters more than the model itself. Side Hustle School Ep. 3433.
- Q&A: "How many income streams is best?"
How many income streams should you build? Best practices for balancing multiple side hustles without overextending yourself. Side Hustle School Ep. 3430.
- Q&A: "Is there a template to make an app or other software?"
Can you build a marketplace app without coding? Finding templates and no-code tools for Craigslist-Airbnb hybrids. Side Hustle School Ep. 3427.
- Q&A: "Should I provide a guarantee for my real estate photography service?"
Real estate photography guarantees: Should you offer one and how to structure it. Side Hustle School Ep. #3426.
- Q&A: "How can I compete with unfair Etsy sellers?"
How to compete with sellers breaking Etsy's handmade rules. Strategies for honest sellers facing unfair competition. Side Hustle School Ep. 3423.
- Q&A: "Have I found a way to accept PayPal payments with no fees?"
How to accept PayPal payments without fees—and why a popular workaround might backfire. Side Hustle School Ep. 3420.
- Q&A: "How to grow a facepainting business?"
How to grow a facepainting business by bundling services and selling more to existing customers. Side Hustle School Ep. 3419.
- Q&A: "Is it still a good idea to sell Merch by Amazon?"
Is Merch by Amazon still worth it? Learn if print-on-demand t-shirt design is viable and key strategies to succeed. Side Hustle School Ep. 3416.
- Q&A: "How can I sell my own crossword puzzles?"
How to sell crossword puzzles to fans beyond the New York Times monopoly. Find your niche audience and pricing strategy. Side Hustle School Ep. 3413.
- Q&A: "How to share men's lifestyle advice that isn't toxic…"
How to share men's lifestyle advice without toxicity or politics. Positioning advice for building an authentic brand. Side Hustle School Ep. 3412.
- Q&A: "I bought and sold 75 Peloton bikes…"
Reselling 75 Peloton bikes at $250 profit each during the pandemic. How arbitrage timing turned a trend into $18,750. Side Hustle School Ep. 3409.
- Q&A: "I want to make an asexual dating app…"
Building an asexual dating app: niche community needs, existing platform options, and launch strategy advice. Side Hustle School Ep. 3406.
- Q&A: "I'm making an alarm clock that costs money if you oversleep…"
Alarm clock that charges you money if you oversleep—how to turn this idea into reality. Side Hustle School Ep. 3405.
- Q&A: "Need to increase income as an adjunct professor…"
Adjunct professor earning under $3,000 per course seeks ways to leverage sociology expertise for extra income. Side Hustle School Ep. 3402.
- Q&A: "Is my business idea a pyramid scheme?"
How to tell if your business idea is a pyramid scheme—and what makes the difference. Side Hustle School Ep. 3399.
- Q&A: "How to go from prototype into manufactured product?"
How to turn a product prototype into manufactured goods for retail. Manufacturing sourcing and assembly strategies for makers. Side Hustle School Ep. 3398.
- Q&A: "An old-school magazine about old-school businesses…"
Can a print-only magazine about vintage business advice work in 2024? Exploring the viability of old-school publishing. Side Hustle School Ep. #3395.
- Q&A: "Should I use Etsy's new platform or build my own website?"
Etsy Pattern vs. your own website: which platform is best for growing your monogramming business. Side Hustle School Ep. 3392.
- Q&A: "Should I quit my job when the economy is bad?"
Should you quit your job during an economic downturn? Weigh your options with key questions to ask yourself. Side Hustle School Ep. 3391.
- Q&A: "Someone left me a bad review! What should I do??"
Bad Etsy review unfair? Learn if you can appeal it, work with the reviewer, or move forward. Side Hustle School Ep. 3388.
- Q&A: "What if a company hires you and doesn't pay up??"
What to do if a company hires you and doesn't pay. How to protect yourself with contracts and invoicing strategies. Side Hustle School Ep. 3385.
- Q&A: "I'm running the numbers on a subscription service…"
Subscription pricing for a nutrition app at $5/month: can you hit 2,000 customers for sustainable recurring revenue? Side Hustle School Ep. 3384.
- Q&A: "Driving an RV across the country—can I get sponsored?"
- Q&A: "Help, my bank said I can't open a business account!"
- Q&A: "Should I create a website for medical coders?"
- Q&A: "Should I offer a pay-what-you-will price?"
- Q&A: "Any tips for buying stuff at flea markets to resell?"
- Q&A: "Can I tell people where to find fake luxury goods?"
- Q&A: "I'm ready for more passive income…"
- Q&A: "Can I use other people's recipes in my children's ebook?"
- Q&A: "Should I start a podcast or a YouTube channel?"
- Q&A: "How to start a meal prep side hustle?"
- Q&A: "How can I get paid to help resellers?"
- Q&A: "I'm a professional speed skater. How can I fundraise?"
- Q&A: "One-page business plan: what is the essential info?"
- Q&A: "What are the most profitable niches for teaching?"
- Q&A: "I'm opening a new hair salon. How can I build my clientele?"
- Q&A: "I'm being headhunted... for my side hustle!"
- Q&A: "How to break out of a sales slump?"
- Q&A: "What's the best way to register domains?"
- Q&A: “What kind of review platform would be best for online learning?”
- Q&A: “Is there a way to trade plane tickets for profit?”
- Q&A: “What separates small earners from big ones?”
- Q&A: “How to sell a reusable fork…”
- Q&A: “Should I pay a publicist to book me as a podcast guest?”
- Q&A: “Why do online courses cost so much—or so little?”
- Q&A: “How can I become a personal finance influencer?”
- Q&A: “Can I import rain barrels from the Netherlands?”
- Q&A: “Should I start a new business or expand my current one?”
- Q&A: “How can I sell on a platform like NextDoor?”
- Q&A: “How do I transition from Etsy to Shopify?”
- Q&A: “What’s the best software to write a non-fiction book?”
- Q&A: “Get paid to help brands with their Terms & Conditions?”
- Q&A: “What are the ethics of paid referrals to therapists?”
- Q&A: “Should I charge a flat fee or percentage?”
- Q&A: “Is it better to have more projects or a single focus?”
- Q&A: “How do songs get licensed for background music?”
- Q&A: “How many ‘wine-of-the-month’ clubs are there??”
- Q&A: “Should I pay $2,000 for a domain name I really want?”
- Q&A: “I’m offering executive coaching at a high price…”
- Q&A: “How can an author succeed these days?”
- Q&A: “What if you don’t want to use social media?”
- Q&A: “After 8 years of daily episodes, what’s next?”
- Q&A: “How can I keep from negotiating against myself?”
- Q&A: “How do I raise rates without losing clients?”
- Q&A: “Do I have to be loud to sell my service?”
- Q&A: “Can I I force myself to ship something every two weeks?”
Today's caller is stuck in study-hall mode. We'll set a simple “learn 30%, build 70%” rule and a launch checkpoint, so that progress… Side Hustle...
- Q&A: “How do I talk about pricing when it feels impolite?”
- Q&A: “How do I avoid a bad review on my first client job?”
- Q&A: “Should I have a logo before I launch?”
- Q&A: “Are Instagram links killing my reach?”
- Q&A: “Should I add shipping to my Marketplace listings?”
- Q&A: “Should I raise my coaching rates or add more clients?”
- Q&A: “Is my struggling side hustle worth saving?”