Education & Tutoring Side Hustles
132 episodes track teachers, tutors, course creators, and education entrepreneurs who found ways to get paid for sharing knowledge. From the music teacher charging $120/hour to the agricultural teacher earning $200K selling lesson plans, education remains one of the highest-trust and highest-margin side hustle categories.
- Failure Friday: "Perfect SAT Score" Tutor Gets Rejected by 100 Publishers
SAT tutor pitched book to 100+ publishers and got rejected. What he learned before launching Prep Expert. Side Hustle School Ep. 3380.
- TBT: Best Guitar Lessons in the Universe
University administrator built sustainable full-time income teaching guitar lessons. Side Hustle School Ep. 3295.
- Agricultural Teacher Earns $200,000 Selling Lesson Plans
How an agricultural teacher earns $200,000 selling lesson plans to educators nationwide. Side Hustle School Ep. 3238.
- Weekend Workshop: The Wandering Teacher’s Global Classroom
Teaching English online to global students. Weekend Workshop series on building 2025 side hustles step-by-step. Side Hustle School.
- First $1,000: Vintage Sewing Machine Rehab Workshops
Vintage sewing machine rehab workshops: buy $20 thrift machines, teach students to restore them, keep the working Singer. Side Hustle School Ep. 3208.
- TBT: Helping High School Dropouts Start Plumbing Careers
Helping high school dropouts start plumbing careers through trade school partnerships. One side hustler's path to impact. Side Hustle School Ep. 3176.
- Q&A: “How do I license my educational materials to a publisher?”
How to license educational materials to publishers for passive income and wider reach. Side Hustle School Ep. 3125.
- High School Student Earns $20,000 Making Wooden Bow Ties
High school student earns $20,000 selling wooden bow ties. Started after receiving one as a gift and decided to make his own. Side Hustle School Ep. 3070.
- TBT: Missoula Videographer Redefines Remote Filming
Videographer ditches travel by mailing filming kits worldwide and directing online course shoots remotely from Missoula. Side Hustle School Ep. 3036.
- Q&A: “How do I create and sell a premium online course?”
How to structure and price a premium online course to stand out in a crowded market. Side Hustle School Ep. 3031.
- Florida Woman Gets Paid to Remove Poisonous Frogs
High school teacher earns $3,000/month removing invasive cane toads across Florida. A ribetting side hustle. Side Hustle School Ep. 3007.
- TBT: Streamlining Standardized Test Preparation
Test prep tutor scales from one-on-one clients to membership platform with guided lessons and practice tests. Side Hustle School Ep. 2994.
- Q&A: “How can I edit course videos efficiently on a budget?”
How to edit online course videos on a budget with beginner-friendly tools. Strategies for sewing course creators. Side Hustle School Ep. 2981.
- Q&A: “Where should I host my online course?”
Where should a history professor host an online course—Udemy or independently? Platform pros and cons for niche topics. Side Hustle School Ep. 2974.
- Q&A: “What’s the best way to offer payment plans?”
Payment plan strategies for online course creators: balancing accessibility with default risks. Side Hustle School Ep. 2947.
- Q&A: “Why did you give away your ‘Doing Things’ course?”
Why give away an online course instead of selling it? Strategy behind free offerings and building audience trust. Side Hustle School Ep. 2920.
- Failure Friday: The Downside of DIY Platforms
Why a course creator's DIY platform backfired—and what went wrong. Side Hustle School Ep. 2820.
- Q&A: “I changed cities and lost my local clients…”
How a math tutor rebuilt her client base after relocating cities. Strategies for local marketing and going online. Side Hustle School Ep. 2717.
- Q&A: “How to turn math tutorials into an online course?”
How to turn math tutorials into an online course. Learn platforms and strategies for launching educational content globally. Side Hustle School Ep. 2657.
- Q&A: “How can I sell my course on female solo travel?”
How to market an online course on female solo travel to a global audience. Essential strategies for standing out. Side Hustle School Ep. 2650.
- Q&A: “Should my online course be live or on demand?”
Live vs. on-demand online courses: which format works best for your teaching style and audience? Side Hustle School Ep. 2626.
- Q&A: “I’m a high-school senior ready to hustle…”
Starting a side hustle as a high school senior: balancing entrepreneurship with college plans and limited resources. Side Hustle School Ep. 2563.
- Failure Friday: The Surprising Impact of Pricing Tiers
Why an online course creator's pricing strategy cost them thousands in lost income. Side Hustle School Ep. 2554.
- Q&A: “An online course for teaching ‘Uncommon Skills…’”
How to create an online course teaching uncommon skills like unicycling and yo-yo tricks. Finding your niche audience. Side Hustle School Ep. 2527.
- Failure Friday: Financial Abundance Coach Charges Too Much
How a financial abundance coach's high pricing strategy backfired with early customers. Side Hustle School Ep. 2519.
- Q&A: “Will my online course cannibalize my freelancing biz?”
Can an online course alongside freelancing work, or will it cannibalize your primary income? Sarah from Boston seeks answers. Side Hustle School Ep. 2492.
- Q&A: “I haven’t sent an invoice in two years…”
How a math tutor moved from cash payments to invoicing after two years. Setting up formal billing for your side hustle. Side Hustle School Ep. 2486.
- Q&A: “A course to help parents learn sign language…”
How to create an online ASL course for parents of infants. Niche market validation and promotion strategies. Side Hustle School Ep. 2460.
- First $1,000: Indian Tutor Helps U.S. High School Students Learn Math
Online math tutor in India earns $1,000 teaching U.S. high school students. How Aman built his first thousand. Side Hustle School Ep. 2389.
- Q&A: “I’m a language tutor… and I need more students!”
Language tutor in Boston struggles to fill her schedule—what marketing strategies work better than social media? Side Hustle School Ep. 2321.
- Failure Friday: ‘Helicopter Parent’ Disrupts Online Tutoring Session
How an online tutoring business fell apart when a helicopter parent disrupted sessions. Side Hustle School Ep. 2253.
- Q&A: “How to create ‘transformational’ online courses?”
How to build transformational online courses that stand out in competitive markets. What makes courses work today. Side Hustle School Ep. 2215.
- First $1,000: “My sister and I made this game to honor our dad…”
Sisters create board game and app about stars to honor their dad. How they hit their first $1,000. Side Hustle School Ep. 2116.
- Head-to-Toe Holistic Skincare Biz Shows Moxie
Single mom earns $4,000/month selling small batch holistic skincare from a $150 startup. Ancient Egypt inspired her formulas. Side Hustle School Ep. 1963.
- Q&A: “How can I grow my podcast without social media?”
Growing a podcast without social media: strategies for reaching Gen Z audiences. Side Hustle School Ep. 1940.
- “Free Prep Course” Site Generates 7-Figure Income
How a former educator built a 7-figure test prep site by giving courses away free and monetizing through ads. Side Hustle School Ep. 1865.
- Rustic Tiki Bars Turn Into Pallet-able Career
How a teaching grad earns $8,000/month building custom rustic tiki bars from pallets for homeowners. Side Hustle School Ep. 1788.
- TBT: Tap Dance Teacher Offers Worldwide Lessons
Tap dance teacher earns six figures teaching worldwide from Melbourne, Australia via HowtoTapDance.com. Side Hustle School Ep. 1776.
- Q&A: Best platform to host an online course?
Which platform is best for hosting your online course? Comparing Thinkific, Teachable, Kajabi, and more. Side Hustle School Ep. 1775.
- Q&A: “I’d like to create a cohort-based course like B-School”
Cohort-based courses: advantages and disadvantages for creators earning $140,000+. Why some courses close between sessions. Side Hustle School Ep. 1736.
- 7th Grade Teacher Earns 2nd Income Writing Resumes
English teacher earns side income writing resumes on Upwork. Greg Marano uses his writing skills to help job seekers. Side Hustle School Ep. 1730.
- Lawyer Moonlights Music Production Tutorials
Lawyer earns $2,000/month teaching music production tutorials on YouTube. Shares wisdom on handling online trolls. Side Hustle School Ep. 1697.
- ESL Teacher Resells Furniture for Big Profits
ESL teacher flips furniture for $5,000/month income. Started by reselling barstools on Facebook Marketplace. Side Hustle School Ep. 1688.
- Tumultuous Relationship Leads to Togetherness Blog
Couple builds relationship blog and coaching service after breaking up three times and learning to communicate better. Side Hustle School Ep. 1667.
- Monogrammed Blanket Etsy Shop Measures Up
Military spouse built six-figure Etsy blanket shop with $100 machine, sold 20,000+ items. Side Hustle School Ep. 1613.
- Intern Manages Businesses For Six-Figure Income
How an intern manages businesses for $8000/month and creates her own job title. Side Hustle School Ep. 1611.
- Failure Friday: “I didn’t know what I didn’t know…”
Voiceover artist earned $500k with actor app, then failed at online courses. What went wrong and why. Side Hustle School Ep. 1581.
- Emergency Room PA Creates Medical Spanish Course
How an ER PA earns $55k/year with a medical Spanish course. Combines expertise in emergency medicine and fluent Spanish. Side Hustle School Ep. 1578.
- TBT: Multilingual Insurance Agent Creates Translation Course
Multilingual insurance agent earns $40,000/year with online translation course. Jennifer updates her side hustle story. Side Hustle School Ep. 1552.
- CLASSROOM: Revisiting Key Lessons (Part II)
Key lessons on persuasion, content creation, psychographics, and family support for side hustlers. Side Hustle School Ep. 1444.
- Q&A: Help! I’m still overwhelmed with buying products on Alibaba
Alibaba vs. Alibaba Express: which platform should you use for product sourcing? Clear answers to common confusion. Side Hustle School Ep. 1432.
- CLASSROOM: Revisiting Key Lessons (Part I)
Key lessons from 2020 Classroom episodes: idea validation, time management, and practical startup strategies. Side Hustle School Ep. 1430.
- Q&A: Should I publish my course in more than one location?
Should you publish your online course on multiple platforms like Udemy and Coursera, or stick with one? Side Hustle School Ep. 1425.
- Q&A: Should I change my business name?
Should you rebrand your side hustle? A gardener earning $400/month from his online course weighs rebranding options. Side Hustle School Ep. 1418.
- CLASSROOM: Troubleshooting—What If It Doesn’t Work?
How to troubleshoot when your side hustle fails. Face the problem and turn missteps into momentum. Side Hustle School Ep. 1416.
- CLASSROOM: Sourcing Products Using Alibaba
Six tips for sourcing products from Alibaba and AliExpress to buy and resell. Learn B2B vs B2C differences. Side Hustle School Ep. 1402.
- Pharmacist Provides Formula For Aspiring Technicians
Pharmacist earns $2,000/month selling pharmacy tech certification courses online. Side Hustle School Ep. 1401.
- CLASSROOM: Dealing with Customer Complaints
How to handle customer complaints without getting overwhelmed. Three strategies to keep customers happy and stay sane. Side Hustle School Ep. 1388.
- College Curriculum Developer Makes Minimalist Jewelry
How a college curriculum developer earns $10,000 annually making minimalist jewelry. Her first sale gave her the chills. Side Hustle School Ep. 1375.
- CLASSROOM: Transitioning Between Projects
Managing multiple projects without losing focus: strategies for transitioning between your day job and side hustle. Side Hustle School Ep. 1374.
- CLASSROOM: How to Ask for Referrals
How to ask for referrals and build a steady stream of customers from your existing client base. Side Hustle School Ep. 1360.
- CLASSROOM: Crowdfunding Basics & Best Practices
Crowdfunding basics for product launches: money, validation, and best practices for running a successful campaign. Side Hustle School Ep. 1332.
- Former High School Athlete Creates Coaching Subscription
How a sales VP built a $100K/year coaching subscription teaching leadership to high school athletes. Side Hustle School Ep. 1319.
- CLASSROOM: Set Up a WordPress Website
Build your first WordPress website in minutes without spending much money. Done is better than perfect. Side Hustle School Ep. 1318.
- Q&A: How can I drive more traffic to my site instead of Udemy?
How to drive traffic to your own site instead of Udemy. Arnold's home improvement course earns $100k profit. Side Hustle School Ep. 1313.
- CLASSROOM: Create Content By Answering Questions
Find what your ideal customers search for and create content by answering their questions. SEO strategy for side hustles. Side Hustle School Ep. 1304.
- CLASSROOM: Forecast Your Profit on a Napkin
How to forecast profit on a napkin using simple math: expected income minus expenses equals projected profit. Side Hustle School Ep. 1290.
- CLASSROOM: How to Avoid Getting Stuck
Five tips to avoid getting stuck in your side hustle before it happens. Mental blocks and practical solutions. Side Hustle School Ep. 1276.
- CLASSROOM: Dealing with Unsupportive Family Members
How to handle unsupportive family when building your side hustle. Balance your dreams with the relationships you value most. Side Hustle School Ep. 1269.
- CLASSROOM: Halfway through the year! Let’s review.
Midyear review of Classroom series: idea selection, product development, and next focus on marketing. Side Hustle School Ep. 1262.
- CLASSROOM: Who Are “Your People”? Understanding Psychographics
Understanding psychographics: identifying ideal customers by values and beliefs, not just age or location. Side Hustle School Ep. 1255.
- CLASSROOM: Create a Powerful Origins Story
Craft a compelling origin story for your side hustle that connects your unique abilities to customer problems. Side Hustle School Ep. 1248.
- CLASSROOM: Using Automation & Workflows
How to work smarter using automation and workflows. Simplify manual processes with tools like Keyboard Maestro. Side Hustle School Ep. 1241.
- CLASSROOM: Design a Smart Launch Strategy
Design a smart product launch strategy. Learn how to plan your launch for long-term success, not just first-week sales. Side Hustle School Ep. 1234.
- CLASSROOM: Pros and Cons of The Funnel Model
Sales funnel pros and cons: low-price entry, upsells, and scale. When does the model work for your business? Side Hustle School Ep. 1227.
- English Teacher Writes His Way Into All-Star Tutoring
NYC English teacher becomes top-rated writing tutor by niching down. How specialization beats the crowded tutoring market. Side Hustle School Ep. 1226.
- CLASSROOM: How Will You Fulfill Orders?
Build a fulfillment plan for products or services before orders arrive. How to deliver confidently and scale efficiently. Side Hustle School Ep. 1220.
- CLASSROOM: Questions to Ask Manufacturers and Vendors
Essential questions to ask manufacturers and vendors before partnering on product development. Side Hustle School Ep. 1213.
- CLASSROOM: The 6 Factors of Persuasion, Part II
The 6 factors of persuasion part II: liking, reciprocity, scarcity. Psychological principles to boost sales. Side Hustle School Ep. 1206.
- CLASSROOM: The 6 Factors of Persuasion, Part I
The psychology behind why people make purchasing decisions. Learn six persuasion factors to boost your side hustle sales. Side Hustle School Ep. 1199.
- CLASSROOM: The Power of Your Own Small Army
How to leverage your social network to promote products and services authentically. Side Hustle School Ep. 1192.
- CLASSROOM: Side Hustle Sprint! It’s Time to Break Out the Duct Tape
Launch your side hustle in two weeks or less. What do you really have to do, and what are you putting off? Side Hustle School Ep. 1185.
- TBT: Best Guitar Lessons in the Universe
Guitar teacher builds full-time income with systematic marketing approach. Jake's story at Severn River Guitar. Side Hustle School Ep. 1181.
- CLASSROOM: Don’t Listen to This Boring Episode
Business licenses, bank accounts, and record-keeping essentials for side hustlers. Set up systems early to avoid stress later. Side Hustle School Ep. 1178.
- CLASSROOM: Finding Time to Work on Your Hustle
Find time for your side hustle by stopping time-wasters, planning your work sessions, and focusing on what matters. Side Hustle School Ep. 1171.
- CLASSROOM: The MVP of Minimum Viable Products
What's the minimum viable product you really need to launch in 30-90 days? Learn the essential MVP elements. Side Hustle School Ep. 1164.
- CLASSROOM: Give The People What They Want
Listen to your customers and find out what they really want, not what you think they need. Side Hustle School Ep. 1157.
- CLASSROOM: Three Elements of Every Strong Offer
The three elements of every strong offer: a promise, a pitch, and a price. Build compelling offers customers can't ignore. Side Hustle School Ep. 1150.
- TBT: YouTube Tutorials Help Immigrants Gain Citizenship
Mom earns six figures teaching US citizenship on YouTube to immigrants. Free lessons, massive subscriber growth. Side Hustle School Ep. 1146.
- CLASSROOM: It’s Not Just What You Say, It’s How You Say It
Branding and messaging are core components of product design. How you talk about your product matters. Side Hustle School Ep. 1143.
- CLASSROOM: Roadmap to Launch (What Lies Ahead)
Plan your side hustle launch in phases: idea, preparation, and launch. Learn what you need to do now to succeed. Side Hustle School Ep. 1136.
- CLASSROOM: Avoiding Mistakes in the Idea Phase
Seven common mistakes in the side hustle idea phase and how to avoid them—from vague messaging to unclear revenue models. Side Hustle School Ep. 1129.
- CLASSROOM: Deciding on an Idea
How to choose the right side hustle idea when you have multiple options. A practical framework for deciding. Side Hustle School Ep. 1122.
- CLASSROOM: Different Categories of Side Hustles
Products vs. services: which side hustle category fits your business idea? Learn how to classify your concepts. Side Hustle School Ep. 1115.
- CLASSROOM: Four Ways to Identify Moneymaking Ideas
Four ways to identify moneymaking side hustle ideas: notice problems, ask questions, observe gaps, and test assumptions. Side Hustle School Ep. 1108.
- CLASSROOM: Goals, Agenda, and Your First Assignment
Set your side hustle goal for 2020. Learn why defining your objective matters before starting. Side Hustle School Ep. 1101.
- Art Teacher Draws Her Way Into Ceramic Shop
How an art teacher earns $600/month selling handmade ceramic touchstones. She borrowed a laser to test her idea first. Side Hustle School Ep. 1071.
- High School Teacher Starts Baseball Pitching Academy
How a high school teacher built a six-figure baseball pitching academy with flyers and word-of-mouth. Side Hustle School Ep. 1005.
- WEEKLY RECAP: How to Design a Profitable Online Course
Weekly recap: online course design, hand-drawn greeting cards, and Kickstarter success — with profitable course strategies. Side Hustle School Ep. 988.
- Dance Teacher Launches Toe Tapping Online Course
Tap dance teacher launches online course after overcoming self-doubt. Proved it's never too late to build a new revenue stream. Side Hustle School Ep. 982.
- Cuban Journalist Teaches Everyday Spanish Classes
Cuban journalist teaches Spanish classes using humor and real-world phrases to help students retain the language faster. Side Hustle School Ep. 962.
- Blogger Earns $140,000 from Beta Phase of Online Course
How a blogger earns $140,000 from her online course beta on rental properties. Eight investment properties by age 34. Side Hustle School Ep. 961.
- Hawaiian Native Teaches Virtual Ukulele Lessons
Hawaiian native teaches virtual ukulele lessons globally via Skype, touring Europe while building a remote music business. Side Hustle School Ep. 938.
- Former White House Aide Teaches People to Make Friends
Former White House aide teaches relationship building skills through a profitable blog and LinkedIn strategy. Side Hustle School Ep. 894.
- High School Teacher Spins His Way to Profits
Vinyl record cutting business for a high school teacher. In-person manufacturing spins profits in a niche market. Side Hustle School Ep. 882.
- WEEKLY RECAP: Earning Passive Income with Udemy and LinkedIn
Weekly recap: custom tea brand, social media agency, and six-figure reselling business—plus passive income insights. Side Hustle School Ep. 827.
- Teacher Makes Money Asking Questions Outside the Classroom
High school teacher hosts trivia nights for extra income and earns revenue sharing from other hosts using his equipment. Side Hustle School Ep. 770.
- Vigil Anti-Hacker Logs $110,000 Profit
High school student earns $20,000/month finding computer bugs through ethical hacking. Global hacking events included. Side Hustle School Ep. 766.
- German DJ Turns Up Profits with Magic Marriage Mixes
How a German DJ earns $1,000/month creating custom wedding mixes after ditching a failed online course. Side Hustle School Ep. 642.
- Tie One On for This Australian High School Teacher
How an Australian high school teacher earns $1,000/month selling handmade bow ties. He eventually sells the business itself. Side Hustle School Ep. 629.
- Agricultural Teacher Earns $200,000 Selling Lesson Plans
Agricultural teacher earns $200,000 selling lesson plans to a niche market. Word-of-mouth drives sales in tight-knit community. Side Hustle School Ep. 592.
- Database Expert Helps Students Solve Real Problems
Database consultant Sylvia Moestl Vasilik created an online course and book to teach SQL Server skills. Side Hustle School Ep. 570.
- English Teacher Turns Passion for Verbs Into Online Income
ESL teacher creates a game teaching phrasal verbs to English learners. Features 70 common verb combinations. Side Hustle School Ep. 499.
- Doctor Does Off-Hours Voiceover Work to Pay Med School Bills
Doctor earns $2,000/month doing voiceover work for major brands while paying med school debt. Trained his ear by studying ads. Side Hustle School Ep. 489.
- Adjunct Professor Puts Course on YouTube for $100k Profit
How an adjunct professor earns $100k profit selling cyber security courses on Udemy. 35,000 students in 16 months. Side Hustle School Ep. 462.
- It’s Not Vandalism, It’s a $15,000 Yard-Gram Hustle
School teacher earns $15,000/year placing pink flamingos in neighbors' yards for Yard-Grams. Word-of-mouth buzz pays off. Side Hustle School Ep. 436.
- High School Student Earns $20,000 Making Wooden Bow Ties
How a high school student earns $20,000 making wooden bow ties on Etsy. Started after receiving one as a gift. Side Hustle School Ep. 423.
- ESL Teacher Turned Travel Planner Sends Clients on Surprise Vacations
Surprise travel planner books mystery vacations for clients. How an ESL teacher built a service selling unforgettable trips. Side Hustle School Ep. 346.
- Florida Woman Gets Paid to Remove Poisonous Frogs
High school science teacher earns $3,000/month removing invasive Bufo toads in Florida. Side Hustle School Ep. 332.
- Substitute Teacher Earns $1,500/Month Making Wooden Signs
Substitute teacher earns $1,500/month making wooden pallet signs at DIY craft parties. Host stencil-based workshops for groups. Side Hustle School Ep. 314.
- Published Author Adds Income Source; Makes Additional $21,000 Her First Year
Published author earns $21,000 teaching online writing courses to 3,700 students. Productivity course on Udemy. Side Hustle School Ep. 303.
- Lawyer Creates Online Course for Mothers Returning to Work
DC lawyer creates online course for mothers returning to work, earning $2,000/month. Employers now pay for it. Side Hustle School Ep. 255.
- Language Teacher Becomes Fluent In Passive Income
How a language teacher earns $500/month in passive income from audio lessons. Creates courses from classroom material. Side Hustle School Ep. 243.
- High School Junior Earns $10,000 Selling Autographed Baseballs
How a high school junior earns $20,000 selling autographed baseballs. Tim Haren's baseball memorabilia side hustle. Side Hustle School Ep. 212.
- High School Teacher Turns Woodworking Hobby Into a 5-Figure Side Hustle
High school teacher earns $25,000 with wooden jewelry side hustle. Craft show success after online flops. Side Hustle School Ep. 203.
- High-School French Teacher Earns $8,000 Writing & Selling Curriculum
How Erin earns $8,000/year selling French curriculum on Teachers Pay Teachers. 600+ digital products, royalty income. Side Hustle School Ep. 142.
- College Lecturer Makes Money by Helping Other Instructors Teach Better
How a college lecturer earns $31,000 coaching other instructors on curriculum building and classroom success. Side Hustle School Ep. 72.
- Elementary School Teacher Pans for Gold in New Zealand
Elementary teacher earns $40,000/year selling handmade jewelry at Queenstown Market in New Zealand. Side Hustle School Ep. 62.
- PE Teacher Makes $11,000 with Membership Site
PE teacher earns $11,000 with membership site for teacher resources. Ben's annual membership model replaced low-price PDFs. Side Hustle School Ep. 59.
- Facebook Photo Leads to Today Show Appearance
Non-toxic face paint for school events built by a teacher frustrated with toxic alternatives. Featured on TODAY show. Side Hustle School Ep. 52.
- Guitar Teacher Sells Lessons on Craigslist and Makes $80/Hour
Guitar teacher earns $80/hour on Craigslist, scales to $5-6K/month. Pricing strategy. Side Hustle School Ep. 23.
- 17-Year Old Canadian Makes $7,000 from Holiday Pop-Up Shop
How a 17-year-old Canadian earned $7,000 from a holiday pop-up shop selling cosmetics at the mall. Side Hustle School Ep. 22.