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: "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?"
How to get RV trip sponsorships while traveling with family across the country. Monetizing your van life journey. Side Hustle School Ep. 3381.
- Q&A: "Help, my bank said I can't open a business account!"
Why your bank rejected your business account application and what to do next. Side Hustle School Ep. 3378.
- Q&A: "Should I create a website for medical coders?"
Should medical coders need a website for CE credits? Monetizing continuing education for licensed professionals. Side Hustle School Ep. 3377.
- Q&A: "Should I offer a pay-what-you-will price?"
Pay-what-you-will pricing for a calligraphy snail mail service: should you use it? Q&A on scaling. Side Hustle School Ep. 3374.
- Q&A: "Any tips for buying stuff at flea markets to resell?"
How to buy items at flea markets and resell them for profit. Tips for finding inventory and avoiding unsellable stock. Side Hustle School Ep. 3371.
- Q&A: "Can I tell people where to find fake luxury goods?"
Can you legally connect buyers with counterfeit luxury goods? Legal risks explained. Side Hustle School Ep. 3370.
- Q&A: "I'm ready for more passive income…"
How to scale side hustles toward passive income when you're already earning $50,000/year. Strategies for reducing active work. Side Hustle School Ep. 3367.
- Q&A: "Can I use other people's recipes in my children's ebook?"
Can you legally use recipes found online in your children's ebook? Copyright and attribution rules explained. Side Hustle School Ep. 3364.
- Q&A: "Should I start a podcast or a YouTube channel?"
Podcast vs YouTube channel: which format fits your teaching goals? Learn the pros, cons, and decision framework. Side Hustle School Ep. 3363.
- Q&A: "How to start a meal prep side hustle?"
How to turn meal prepping into a profitable side hustle. Monetizing your cooking skills beyond meal delivery services. Side Hustle School Ep. 3360.
- Q&A: "How can I get paid to help resellers?"
Selling products to resellers instead of competing as one yourself. Learn the "gold rush shovel" strategy. Side Hustle School Ep. 3357.
- Q&A: "I'm a professional speed skater. How can I fundraise?"
How a speed skater can fundraise for Olympic training through products and social media. Side Hustle School Ep. #3356.
- Q&A: "One-page business plan: what is the essential info?"
What makes a one-page business plan work and what essential info should you include. Side Hustle School Ep. 3353.
- Q&A: "What are the most profitable niches for teaching?"
What niches are most profitable for teaching and what they have in common. Learn which topics earn the most. Side Hustle School Ep. 3350.
- Q&A: "I'm opening a new hair salon. How can I build my clientele?"
Building clientele for a new hair salon: leverage existing clients and tap local community. Side Hustle School Ep. 3349.
- Q&A: "I'm being headhunted... for my side hustle!"
Getting headhunted for your side project—when a coding test for programmers attracts unexpected job offers. Side Hustle School Ep. 3346.
- Q&A: "How to break out of a sales slump?"
How to break out of a sales slump in your side hustle. Actionable strategies for regaining momentum when business hits a lull. Side Hustle School Ep. 3343.
- Q&A: "What's the best way to register domains?"
Domain registration basics: choosing registrars, extensions, and avoiding $150/year overspend. Side Hustle School Ep. 3342.
- Q&A: “What kind of review platform would be best for online learning?”
Building a review site for online courses: choosing the right platform to launch with user-generated reviews. Side Hustle School Ep. 3339.
- Q&A: “Is there a way to trade plane tickets for profit?”
Can you resell plane tickets with different names? Exploring the legal and practical barriers to a ticket-trading side hustle. Side Hustle School Ep. 3336.
- Q&A: “What separates small earners from big ones?”
What separates small earners from big ones in side hustles? Learn the skills and strategies behind six-figure earners. Side Hustle School Ep. 3335.
- Q&A: “How to sell a reusable fork…”
Finding your ideal customer for an eco-friendly utensil product. Tips for selling Fork in the Rose reusable eating sets. Side Hustle School Ep. 3332.
- Q&A: “Should I pay a publicist to book me as a podcast guest?”
Should you hire a publicist to book podcast guest appearances as a lifestyle coach? Get the answer and better alternatives. Side Hustle School Ep. 3329.
- Q&A: “Why do online courses cost so much—or so little?”
Why do online courses cost $50 or $3,000+? Learn how to price your course right. Side Hustle School Ep. 3328.
- Q&A: “How can I become a personal finance influencer?”
Breaking into personal finance content creation as a crowded market. How to find your angle and start. Side Hustle School Ep. 3325.
- Q&A: “Can I import rain barrels from the Netherlands?”
Can you become a U.S. distributor for Dutch-made rain barrels? How to approach product distribution partnerships. Side Hustle School Ep. 3322.
- Q&A: “Should I start a new business or expand my current one?”
Should you expand your current business or launch a new one? Four key factors to consider for entrepreneurs ready to grow. Side Hustle School Ep. 3321.
- Q&A: “How can I sell on a platform like NextDoor?”
How to sell on NextDoor: what works, what doesn't, and whether it's a viable sales channel for your business. Side Hustle School Ep. 3318.
- Q&A: “How do I transition from Etsy to Shopify?”
Moving your Etsy shop to Shopify: setup tips, avoiding decision fatigue, and when to make the leap. Side Hustle School Ep. 3315.
- Q&A: “What’s the best software to write a non-fiction book?”
What's the best software to write a non-fiction book? We share three tools to make writing easier, plus what to avoid. Side Hustle School Ep. 3314.
- Q&A: “Get paid to help brands with their Terms & Conditions?”
Terms & Conditions templates for brands: Can you license simplified T&C templates to companies? Side Hustle School Ep. 3311.
- Q&A: “What are the ethics of paid referrals to therapists?”
Ethics of paid referrals to therapists on YouTube: balancing commission potential with professional responsibility. Side Hustle School Ep. 3308.
- Q&A: “Should I charge a flat fee or percentage?”
Flat fee or percentage for consignment sales? Learn pricing strategies for selling items on behalf of others. Side Hustle School Ep. 3307.
- Q&A: “Is it better to have more projects or a single focus?”
Multiple side hustles or single focus: which strategy works best for your goals. Side Hustle School Ep. 3304.
- Q&A: “How do songs get licensed for background music?”
How songs get licensed for background music in retail stores—and why it pays better than Spotify. Side Hustle School Ep. 3301.
- Q&A: “How many ‘wine-of-the-month’ clubs are there??”
Subscription box and "of-the-month" clubs: market saturation or untapped demand? What makes the monthly club model work. Side Hustle School Ep. 3300.
- Q&A: “Should I pay $2,000 for a domain name I really want?”
Is a $2,000 domain name worth it for your new business? We break down the decision. Side Hustle School Ep. 3297.
- Q&A: “I’m offering executive coaching at a high price…”
How to position and price executive coaching for high performers. Addressing clarity on benefits and premium pricing strategy. Side Hustle School Ep. 3294.
- Q&A: “How can an author succeed these days?”
How can an author succeed in today's market? Publishing strategies for selling your first novel as a series. Side Hustle School Ep. 3293.
- Q&A: “What if you don’t want to use social media?”
Can you build a motion video business for churches without social media? Learn alternatives to reach your audience. Side Hustle School Ep. 3290.
- Q&A: “After 8 years of daily episodes, what’s next?”
What's next for Side Hustle School after 8 years? Chris shares the podcast's tenth-year plans and upcoming experiments. Side Hustle School Ep. 3286.
- Q&A: “How can I keep from negotiating against myself?”
How to stop undercutting your own price before clients object. Fix the habit with structure, not willpower. Side Hustle School Ep. 3283.
- Q&A: “How do I raise rates without losing clients?”
Raise your rates without losing clients: value assessment, pricing timeline, and client communication strategy. Side Hustle School Ep. 3282.
- Q&A: “Do I have to be loud to sell my service?”
Low-noise marketing tactics for introverts selling services. Build quiet credibility without daily social media posting. Side Hustle School Ep. 3279.
- 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?”
Overcome guilt about pricing in your service business. Reframe selling as offering structured value, not asking for money. Side Hustle School Ep. 3275.
- Q&A: “How do I avoid a bad review on my first client job?”
Manage first client risk: clear scope, midpoint check-ins, and fast fixes to prevent bad reviews. Side Hustle School Ep. 3272.
- Q&A: “Should I have a logo before I launch?”
When should you design a logo for your side hustle? Learn if early branding helps or hurts product validation. Side Hustle School Ep. 3269.
- Q&A: “Are Instagram links killing my reach?”
How Instagram's algorithm affects external links and which native tools keep your reach high while driving sales. Side Hustle School Ep. 3268.
- Q&A: “Should I add shipping to my Marketplace listings?”
Should you add shipping to Marketplace listings? When it's worth it, payment safety, and a low-risk pilot approach. Side Hustle School Ep. 3265.
- Q&A: “Should I raise my coaching rates or add more clients?”
Coaching rate increase or more clients? We'll show the math on pricing vs. volume for solo coaches at capacity. Side Hustle School Ep. 3262.
- Q&A: “Is my struggling side hustle worth saving?”
When your side hustle earns $600 in eight months, how do you know if it's worth saving? A 90-day experiment to decide. Side Hustle School Ep. 3261.
- Q&A: “Can I profit from flipping open-box customer returns?
How to flip open-box returns for profit: evaluate pallets, calculate true margins, avoid dead inventory. Side Hustle School Ep. 3258.
- Q&A: “When is uneven side-hustle income safe to rely on?”
When is uneven side-hustle income safe to rely on? Learn the safety signals and cash-flow tactics for quitting your day job. Side Hustle School Ep. 3255.
- Q&A: “How do I price my VA work for true value?”
How do you price VA work for true value instead of hourly rates? Learn the three levers that justify premium pricing. Side Hustle School Ep. 3254.
- Q&A: “Is my burnout a signal to pivot?”
How to tell if burnout means you need rest, a redesign, or a business pivot. Three-question diagnostic for side hustlers. Side Hustle School Ep. 3251.
- Q&A: “Should I spend $2,000 on retention or acquisition?”
Retention vs. acquisition: should your $2K subscription app budget fix churn or chase new users? The math on ROI. Side Hustle School Ep. 3248.
- Q&A: “Instagram, TikTok, or LinkedIn—how do I choose?”
Choosing between Instagram, TikTok, and LinkedIn for your side hustle. A three-question filter to pick your best channel. Side Hustle School Ep. 3247.
- Q&A: “How do I upsell without sounding pushy?”
How to upsell without sounding pushy: frame it as solving problems your client already has. Side Hustle School Ep. 3244.
- Q&A: “Is remote-worker visa consulting a real business?”
Remote-worker visa consulting: pricing, liability, and whether the market is real. Side Hustle School Ep. 3241.
- Q&A: “Should I tell my clients I’m using AI?”
Should you disclose AI use to clients? A practical three-part policy for maintaining trust and quality while using ChatGPT. Side Hustle School Ep. 3240.
- Q&A: “Will professionals trade hours instead of cash?”
Can professionals trade skills instead of cash? Build a fair time-bank model with transparent rules and digital tracking. Side Hustle School Ep. 3237.
- Q&A: “What’s a fair founder-investor deal between friends?”
Founder-investor equity splits between friends: how to structure vesting, dynamic equity, and fair payouts for cash and sweat. Side Hustle School Ep. 3234.
- Q&A: “Where do I find my first paying customer?”
How to land your first paying customer for a side hustle without a network. A concrete plan to turn hobby into revenue. Side Hustle School Ep. 3233.
- Q&A: “How do I test Facebook vs. free traffic?”
How to test Facebook vs. free traffic with a $200 two-week experiment. Design clear go/no-go metrics before scaling ads. Side Hustle School Ep. 3230.
- Q&A: “Why won’t TikTok followers join my newsletter?”
Why TikTok followers won't join your newsletter and the conversion benchmarks that matter. Side Hustle School Ep. 3227.
- Q&A: “Can I legally profit from salvaging barn wood?”
Salvaging barn wood for profit: permits, insurance, and realistic margins. Legal tips for turning reclaimed lumber into cash. Side Hustle School Ep. 3226.
- Q&A: “When does a logo actually matter?”
When to invest in branding versus finishing your product first. A two-checkpoint rule for validating before polishing. Side Hustle School Ep. 3223.
- Q&A: “When is business coaching worth the cost?”
When is business coaching worth the cost? Learn a simple metric to decide if a pricey mentor is a smart bet. Side Hustle School Ep. 3220.
- Q&A: “Can I sell carbon-offset checks to small brands?”
Carbon-offset verification for small brands: design a quick audit service at six figures. Keep client work under two hours. Side Hustle School Ep. 3219.
- Q&A: “How do I avoid a garage full of unsold kits?”
How to avoid a garage full of unsold kits: test demand with preorders before manufacturing. Side Hustle School Ep. 3216.
- Q&A: “Can I monetize a college scholarship database?”
College scholarship database monetization: subscription pricing, data freshness, and credibility strategies. Side Hustle School Ep. 3213.
- Q&A: “Will people pay for AI-optimized resumés?”
Can AI-optimized resumés fill the gap between cheap bots and expensive writers? How to price and prove results. Side Hustle School Ep. 3212.
- Q&A: “How do I use exit pop-ups?”
Exit-intent pop-ups: when to use them and how to avoid training customers to wait for discounts. Side Hustle School Ep. 3209.
- Q&A: “How do I fight preset piracy without hurting buyers?”
Protecting Lightroom presets from piracy without frustrating paying customers. Low-cost deterrents and community strategies. Side Hustle School Ep. 3206.
- Q&A: “How do I license calming coloring pages to wellness apps?”
Licensing coloring pages to wellness apps: pricing, usage rights, and B2B contracts. Side Hustle School Ep. 3205.
- Q&A: “Can a ‘tech deals’ newsletter really make money?”
Can a tech deals newsletter make money? Learn list-building, affiliate math, and trust-building for profitable SaaS curation. Side Hustle School Ep. 3202.
- Q&A: “How do I handle a non-compete that hurts my side hustle?”
How to negotiate non-compete clauses that block your side hustle without damaging your day job. Side Hustle School Ep. 3199.
- Q&A: “I went viral, but now I can’t meet demand!”
Managing viral demand without breaking your business: A four-step triage plan for overwhelmed makers. Side Hustle School Ep. 3198.
- Q&A: “Which passive-income model fits a consultant best?”
Which passive-income model fits a consultant best? Compare courses, content, and compounding assets to escape billing hours. Side Hustle School Ep. 3195.
- Q&A: “How can a freelancer pay herself a stable salary?”
How freelancers can pay themselves a stable salary with a three-bucket system. Turn lumpy income into predictable paychecks. Side Hustle School Ep. 3192.
- Q&A: “What KPIs should I track for my software biz?”
Which KPIs actually matter for micro-SaaS? Cut through dashboard paralysis with the three metrics that drive real decisions. Side Hustle School Ep. 3191.
- Q&A: “Can you run a YouTube channel with only AI voices and scripts?”
Can you run a YouTube channel with only AI voices and scripts? Platform rules, monetization, and audience trust explained. Side Hustle School Ep. 3188.
- Q&A: “How can I sell an Amazon-only FBA brand for top dollar?”
Selling an Amazon FBA brand earning $7,000/month? Reduce channel risk to increase your exit price. Side Hustle School Ep. 3185.
- Q&A: “How can a coast-to-coast road trip pay for itself?”
Make a coast-to-coast road trip pay for itself with portable gigs and location-based hustles. Side Hustle School Ep. 3184.
- Q&A: “Should my first info product be $30 or $300?”
Info product pricing: $30 vs. $300—how to decide based on perceived value and customer quality. Side Hustle School Ep. 3181.
- Q&A: “How do I stop every freelance project from starting in chaos?”
How to build a repeatable freelance onboarding system that eliminates chaos from Day 1—no assistant needed. Side Hustle School Ep. 3178.
- Q&A: “How can I make money by renting out houseplants?
Can you rent out houseplants for profit? Learn the business model for plant staging. Side Hustle School Ep. 3177.
- Q&A: “How can a first-time author stand out in a market of 4,500 books per day?”
How can first-time authors break through when 4,500+ books publish daily? Real numbers and a proven strategy for standing out. Side Hustle School Ep. 3174.
- Q&A: “Managing cash flow across PayPal, Stripe, Venmo, and Etsy…”
How to track PayPal, Stripe, Venmo, and Etsy payments in one system before tax season hits. Side Hustle School Ep. 3171.
- Q&A: “Do followers still matter in the age of algorithms?”
Do follower counts still matter when algorithms control what people see? Learn why subscriber loyalty beats vanity metrics. Side Hustle School Ep. 3170.