Side Hustle School: 2026
October 2026 14 ep.
- 3574 Q&A: “Can I use another author's work in my book?” ⬇
- 3573 Q&A: “How do I focus on retaining clients?” ⬇
- 3572 First $1,000: “I succeeded by following contradictory advice…” ⬇
- 3571 Guitar Player Chalks Up Success By Enjoying The Process ⬇
- 3570 Q&A: “Can I offer a permanent price discount?” ⬇
- 3569 Hand Lettering Artist Upgrades Photo Booth Props ⬇
- 3568 TBT: Physician Designs Plush Toys to Teach Anatomy ⬇
- 3567 Q&A: “Can I resell items I get for free?” ⬇
- 3566 Q&A: “An English-language anime club in Japan…” ⬇
- 3565 First $1,000: “I got paid to walk dogs while on work calls…” ⬇
- 3564 Physical Therapist Sells 57,000 “Neck Hammocks” ⬇
- 3563 Q&A: “What’s the 80/20 rule of side hustling?” ⬇
- 3562 Failure Friday: “My app kept crashing during the big pitch…” ⬇
- 3561 TBT: “Graphic Designer for Dogs” Retrieves New Clients ⬇
September 2026 30 ep.
- 3560 Q&A: "How can I rent out my spare bedroom on Airbnb?" ⬇
- 3559 Q&A: "How to sell a podcast as a paid subscription?" ⬇
- 3558 First $1,000: "Beekeeping is forced zen: be present or get stung!" ⬇
- 3557 Amsterdam Bike Tours Become Passive Profit Center ⬇
- 3556 Q&A: "How to profit from cover songs on Apple Music?" ⬇
- 3555 Continuing Education Directory Earns Six Figures ⬇
- 3554 TBT: Satin Pillowcases Inspire Dreamy Profits ⬇
- 3553 Q&A: "Would you join an introvert's networking club?" ⬇
- 3552 Q&A: "Can you really fly for free as an airline courier?" ⬇
- 3551 First $1,000: "My roommate threw a wad of hundred-dollar bills on the table…" ⬇
- 3550 It's No Joke: Prank Musical Greeting Card Earns $36,000/Month ⬇
- 3549 Q&A: "Should I hire a graphic designer?" ⬇
- 3548 Failure Friday: Supplier Problem Harms Client Relationship ⬇
- 3547 TBT: Bumblebee Linens Builds a New Hive ⬇
- 3546 Q&A: "Where are my customers coming from?" ⬇
- 3545 Q&A: "How can I publish my Army enlistment guide?" ⬇
- 3544 First $1,000: "I have 3 clients and $4,000/month in retainer fees…" ⬇
- 3543 Professor Starts Marvel-ous YouTube Channel ⬇
- 3542 Q&A: "Can you still get paid to post pins on Pinterest?" ⬇
- 3541 "Not Your Grandfather's Scotch": American Woman Starts International Whisky Brand ⬇
- 3540 TBT: Blogger Explores Affiliate Marketing in India ⬇
- 3539 Q&A: "How about a directory of garage and yard sales?" ⬇
- 3538 Q&A: "I have 20 years of experience — how do I pick a niche?" ⬇
- 3537 First $1,000: "I wanted to be the guy with a laptop on the beach…" ⬇
- 3536 BBQ Catering Hustle Smokes Out Competitors ⬇
- 3535 Q&A: "I'm overwhelmed with too many inquiries…" ⬇
- 3534 Failure Friday: "My anniversary sale was an epic fail…" ⬇
- 3533 TBT: "Chewable Energy" Gum Sticks With Customers ⬇
- 3532 Q&A: "I want to be a broker for overseas web developers…" ⬇
- 3531 Q&A: "Can I pursue public speaking as a side hustle?" ⬇
August 2026 31 ep.
- 3530 First $1,000: "I help people get back their hacked accounts…" ⬇
- 3529 Anchors Aweigh! Graphic Designer Leads Guided Sailing Tours ⬇
- 3528 Q&A: "Is it still possible to start a blog?" ⬇
- 3527 Cake Artist's Confections Whisk Up Delicious Profits ⬇
- 3526 TBT: Tap Dance Teacher Offers Worldwide Lessons ⬇
- 3525 Q&A: "Should I self-publish a mental health guidebook on Kindle?" ⬇
- 3524 Q&A: "I'd like to be a financial advisor for Gen Z…" ⬇
- 3523 First $1,000: "I wanted to explore AI-generated art…" ⬇
- 3522 Lather, Rinse, Recycle: Soapy Problem Leads to Clean Solution ⬇
- 3521 Q&A: "How do I find customers as a digital personal assistant?" ⬇
- 3520 Failure Friday: "After I was hit by a car, things got worse…" ⬇
- 3519 TBT: Bridesmaid-for-Hire Keeps Walking Down the Aisle ⬇
- 3518 Q&A: "Where do I begin if I want to make an app?" ⬇
- 3517 Q&A: "Should I start a new site for my food business?" ⬇
- 3516 First $1,000: "I built an Airbnb rental in my backyard…" ⬇
- 3515 Hair Braiding Workshops Help Trans-Racial Adoptive Families ⬇
- 3514 Q&A: "How to make a board game from start to finish?" ⬇
- 3513 Teacher Flips Sports Gear For $8,000/Month ⬇
- 3512 TBT: Southern Transplant Creates Watercolor Brand ⬇
- 3511 Q&A: "Do I have to sell as a SAAS?" ⬇
- 3510 Q&A: "How many tech tools do I need to master?" ⬇
- 3509 First $1,000: Paralegal Assists U.S. Immigrants to Canada ⬇
- 3508 "SwitchPod" Camera Tool Raises $415,748 on Kickstarter ⬇
- 3507 Q&A: "How to convert non-paying students into customers?" ⬇
- 3506 Failure Friday: "I had tears in my eyes reading the response…" ⬇
- 3505 TBT: Family Affirmation Cards Go Global ⬇
- 3504 Q&A: "How do you forecast earnings for a side hustle?" ⬇
- 3503 Q&A: "Ideas for an architect trying to change business models?" ⬇
- 3502 First $1,000: The Pacific Northwest Tiny Home Designer ⬇
- 3501 Networking Success Is Served with a Side of Eggs ⬇
- 3500 Q&A: "What's the best way to sell a digital download?" ⬇
July 2026 31 ep.
- 3499 Hedge Fund Manager Rocks On with Diamond Algorithm ⬇
- 3498 TBT: Hydroponic Indoor Plant System Branches Out ⬇
- 3497 Q&A: "How much time do people spend on these projects?" ⬇
- 3496 Q&A: "Is it ever too early to post on social media?" ⬇
- 3495 First $1,000: Vintage Luggage Upcycler Hits Ground Running ⬇
- 3494 The 50 Shades of Editing Romance Novels ⬇
- 3493 Q&A: "I sold more by raising my prices — is that wrong??" ⬇
- 3492 Failure Friday: "My business partner was a convicted felon…" ⬇
- 3491 TBT: "Kindness Kits" Spread Love and Draw Positive Returns ⬇
- 3490 Q&A: "How can I make a product to help with applied learning?" ⬇
- 3489 Q&A: "I'd like to sell an Apple Watch guide…" ⬇
- 3488 First $1,000: "I had literally zero intention of running a business…" ⬇
- 3487 Chemical Engineer Zips Up Solution for Baggy Shirts ⬇
- 3486 Q&A: "I'd like to sell a toolkit to sole proprietors…" ⬇
- 3485 Atlanta Lawyer Walks Into Food Tour Biz ⬇
- 3484 TBT: Multilingual Insurance Agent Creates Translation Course ⬇
- 3483 Q&A: Are There Any Good MLM Companies? ⬇
- 3482 Q&A: "Recovering after a failed partnership…" ⬇
- 3481 First $1,000: Indian Woman Helps Indian Men Improve Dating Profiles ⬇
- 3480 Aerospace Apprentice Soars to Seven-Figure Heights ⬇
- 3479 Q&A: "Is reselling gift cards a viable idea?" ⬇
- 3478 Failure Friday: "I tried to sell something no one wanted…" ⬇
- 3477 TBT: "Hero's Journal" Completes Epic Quest ⬇
- 3476 Q&A: "How to identify target markets for livestreaming events?" ⬇
- 3475 Q&A: "How to best use a time of unemployment?" ⬇
- 3474 First $1,000: "I had no idea Hula Hoops were a seasonal business…" ⬇
- 3473 Enjoy an Ice Cold Beverage in a Mug Made from Ice ⬇
- 3472 Q&A: "How should I promote my new app?" ⬇
- 3471 Tinder Matched Couple Swipes Right to Sell Cupcakes ⬇
- 3470 TBT: Comfy Pillow Provides Seatbelt Support for Cancer Patients ⬇
- 3469 Q&A: "Where's the best place to hire contractors?" ⬇
June 2026 30 ep.
- 3468 Q&A: "How do you determine a customer's emotional needs?" ⬇
- 3467 First $1,000: "Clients don't want WordPress, they want a website…" ⬇
- 3466 Music Graduate Makes Spare Change Filling Spare Rooms ⬇
- 3465 Q&A: "Help! I'm stuck trying to find my 'ah-ha' idea" ⬇
- 3464 Failure Friday: "We accept your proposal… to resign" ⬇
- 3463 TBT: Beer Made from "Upcycled" Grain ⬇
- 3462 Q&A: "I stopped delivering for my Patreon…" ⬇
- 3461 Q&A: "Should I pursue three ideas or just one?" ⬇
- 3460 First $1,000: Indian Tutor Helps U.S. High School Students Learn Math ⬇
- 3459 Hawaiian Native Teaches Virtual Ukulele Lessons ⬇
- 3458 Q&A: "How do you ethically source products made in overseas factories?" ⬇
- 3457 Financial Blog Sprouts into $35,000/Month Money Tree ⬇
- 3456 TBT: Urban Hiker Leads Tours in San Francisco ⬇
- 3455 Q&A: "My 'road trip kit' for truck stops…" ⬇
- 3454 Q&A: "Which is better: direct or indirect income?" ⬇
- 3453 First $1,000: "My music was played on a Romanian TV show…" ⬇
- 3452 Mental Health Counselor By Day, Headband Artist by Night ⬇
- 3451 Q&A: "'Spaced repetition' practice with overseas tutors?" ⬇
- 3450 Failure Friday: "I decided to give money to Meta…" ⬇
- 3449 TBT: These "Sweatpant Overalls" Produce Joy and Extra Pockets ⬇
- 3448 Q&A: "How to grow a YouTube channel with 121,000 subscribers?" ⬇
- 3447 Q&A: "How can I sell flash cards to pharmacy students?" ⬇
- 3446 First $1,000: Selling Vintage Clothes on Poshmark ⬇
- 3445 Divorce Leads Banker To Boudoir Photography Empire ⬇
- 3444 Q&A: “How do I choose a revenue model for my coaching business?” ⬇
- 3443 Tote-ally Functional Bags for Women on the Go ⬇
- 3442 TBT: Bestselling Author Publishes Novels, Online Courses, and More ⬇
- 3441 Q&A: “Can I file a small claims suit against a big business?” ⬇
- 3440 Q&A: “What's the best platform for my idea?” ⬇
- 3439 First $1,000: Florida Woman Becomes Pet Party Planner ⬇
May 2026 31 ep.
- 3438 Dog Lover Fetches $250,000 in Canine Clothing ⬇
- 3437 Q&A: "How do I best prioritize next steps?" ⬇
- 3436 Failure Friday: "We went all-in on applying for a $2 million grant…" ⬇
- 3435 TBT: 26,000 Handmade Hair Scrunchies ⬇
- 3434 Q&A: "Best way to get to market with nutrition bar…" ⬇
- 3433 Q&A: "Is the directory website model outdated?" ⬇
- 3432 First $1,000: "I wasn't sure what to do, so I started selling sports cards…" ⬇
- 3431 Delaware College Students Place Ads on 450,000 Cars ⬇
- 3430 Q&A: "How many income streams is best?" ⬇
- 3429 Art School Model Starts Sexually Stimulating Side Hustle ⬇
- 3428 TBT: Luxury Buttercream Cakes Make Life Batter ⬇
- 3427 Q&A: "Is there a template to make an app or other software?" ⬇
- 3426 Q&A: "Should I provide a guarantee for my real estate photography service?" ⬇
- 3425 First $1,000: The Med School "Decision Doctor" ⬇
- 3424 Fire in the Hole! Handcrafted Drumsticks Ignite Into Profits ⬇
- 3423 Q&A: "How can I compete with unfair Etsy sellers?" ⬇
- 3422 Failure Friday: "We tried to be everything to everyone…" ⬇
- 3421 TBT: Hair Ties and Shampoo for Men with Long Hair ⬇
- 3420 Q&A: "Have I found a way to accept PayPal payments with no fees?" ⬇
- 3419 Q&A: "How to grow a facepainting business?" ⬇
- 3418 First $1,000: "No one in Boston could find a good pierogi…" ⬇
- 3417 Store Manager Makes Micro Gainz For Macro Profits ⬇
- 3416 Q&A: "Is it still a good idea to sell Merch by Amazon?" ⬇
- 3415 Rustic Wall Hangings Rack Up Worthwhile Profits ⬇
- 3414 TBT: Personal Trainer Pumps Up Protein Pancakes ⬇
- 3413 Q&A: "How can I sell my own crossword puzzles?" ⬇
- 3412 Q&A: "How to share men's lifestyle advice that isn't toxic…" ⬇
- 3411 First $1,000: Software Engineer Crafts Balloon Sculptures ⬇
- 3410 Athletes Create "Chewable Energy" Gum ⬇
- 3409 Q&A: "I bought and sold 75 Peloton bikes…" ⬇
- 3408 Failure Friday: "My Facebook page with 150,000 fans was taken over by hackers…" ⬇
April 2026 30 ep.
- 3407 TBT: Kindle Books Produce Passive Income for Aussie Novelist ⬇
- 3406 Q&A: "I want to make an asexual dating app…" ⬇
- 3405 Q&A: "I'm making an alarm clock that costs money if you oversleep…" ⬇
- 3404 First $1,000: Digital Art Reaches Physical Homes Worldwide ⬇
- 3403 Shoe Designer Runs After $1 Million Challenge ⬇
- 3402 Q&A: "Need to increase income as an adjunct professor…" ⬇
- 3401 Art Director Turns Passion For Puppets Into Profit ⬇
- 3400 TBT: New Jersey Blog Grows to 25+ Team Members ⬇
- 3399 Q&A: "Is my business idea a pyramid scheme?" ⬇
- 3398 Q&A: "How to go from prototype into manufactured product?" ⬇
- 3397 First $1,000: Lutheran Pastor Sells & Ships "Consecrate" Boxes ⬇
- 3396 Loan Officer Charts New Course With Nautically Inspired Jewelry ⬇
- 3395 Q&A: "An old-school magazine about old-school businesses…" ⬇
- 3394 Failure Friday: "I had to issue refunds and cancel 50 orders…" ⬇
- 3393 TBT: Natural Deodorant Becomes Beauty Line ⬇
- 3392 Q&A: "Should I use Etsy's new platform or build my own website?" ⬇
- 3391 Q&A: "Should I quit my job when the economy is bad?" ⬇
- 3390 First $1,000: "I cold-pitched 10 brands and got my first 2 clients…" ⬇
- 3389 Three Friends Step Up, Pull In Restroom Revenue ⬇
- 3388 Q&A: "Someone left me a bad review! What should I do??" ⬇
- 3387 Two Women Create Swimwear Brand for D-Cups and Up ⬇
- 3386 TBT: Texas Marimba Rentals Hit Noteworthy Demand ⬇
- 3385 Q&A: "What if a company hires you and doesn't pay up??" ⬇
- 3384 Q&A: "I'm running the numbers on a subscription service…" ⬇
- 3383 First $1,000: Anime Artist Offers Personalized Commissions ⬇
- 3382 Cigar Subscription Box Delivers Smoking Returns ⬇
- 3381 Q&A: "Driving an RV across the country—can I get sponsored?" ⬇
- 3380 Failure Friday: "Perfect SAT Score" Tutor Gets Rejected by 100 Publishers ⬇
- 3379 TBT: These iPad Paintbrushes Never Run Dry ⬇
- 3378 Q&A: "Help, my bank said I can't open a business account!" ⬇
March 2026 31 ep.
- 3377 Q&A: "Should I create a website for medical coders?" ⬇
- 3376 First $1,000: "I went door-to-door selling home alarms…" ⬇
- 3375 Firefighter Uses Chainsaw for Jumbo-Sized Woodworking ⬇
- 3374 Q&A: "Should I offer a pay-what-you-will price?" ⬇
- 3373 Savvy Stationery Site Offers Cards for Divorce & Diwali ⬇
- 3372 TBT: Frozen Yogurt Dog Treats Are No Barking Matter ⬇
- 3371 Q&A: "Any tips for buying stuff at flea markets to resell?" ⬇
- 3370 Q&A: "Can I tell people where to find fake luxury goods?" ⬇
- 3369 First $1,000: City Government Staffer Leads Virtual Events ⬇
- 3368 Veteran Turns Sweet Compulsion Into Obsessive Candy Hustle ⬇
- 3367 Q&A: "I'm ready for more passive income…" ⬇
- 3366 Failure Friday: "A $300 mistake cost me $100,000" ⬇
- 3365 TBT: YouTube Tutorials Help Immigrants Gain Citizenship ⬇
- 3364 Q&A: "Can I use other people's recipes in my children's ebook?" ⬇
- 3363 Q&A: "Should I start a podcast or a YouTube channel?" ⬇
- 3362 First $1,000: The Canadian Wilderness Experience Curator ⬇
- 3361 Designer Earns $1M Giving It The Old College Try ⬇
- 3360 Q&A: "How to start a meal prep side hustle?" ⬇
- 3359 Working Mother Sells Coats to Buckle in Babies ⬇
- 3358 TBT: Rosary Beads Count Off Extra Income ⬇
- 3357 Q&A: "How can I get paid to help resellers?" ⬇
- 3356 Q&A: "I'm a professional speed skater. How can I fundraise?" ⬇
- 3355 First $1,000: Camping YouTuber Earns Affiliate Income ⬇
- 3354 "Productivity Nannies" Dig Co-Working Caves for Modern Workers ⬇
- 3353 Q&A: "One-page business plan: what is the essential info?" ⬇
- 3352 Failure Friday: "Our first trade show was canceled with no refund…" ⬇
- 3351 TBT: The Tennessee Bachelorette Party Boom ⬇
- 3350 Q&A: "What are the most profitable niches for teaching?" ⬇
- 3349 Q&A: "I'm opening a new hair salon. How can I build my clientele?" ⬇
- 3348 First $1,000: "I earn $3,000/month leading London walking tours…" ⬇
- 3347 Trader Joe's Sign Artist Earns $43,200 Selling Tea-Stained Prints ⬇
February 2026 28 ep.
- 3346 Q&A: "I'm being headhunted... for my side hustle!" ⬇
- 3345 Beard Oil Behemoth Expands to 35 Countries ⬇
- 3344 TBT: iPhone App Tracks Weight-Loss Progress ⬇
- 3343 Q&A: "How to break out of a sales slump?" ⬇
- 3342 Q&A: "What's the best way to register domains?" ⬇
- 3341 First $1,000: “Hyperfluent” Language Service Translates Into Profit ⬇
- 3340 Proud Mainer Brings Whoopie Pies to the World ⬇
- 3339 Q&A: “What kind of review platform would be best for online learning?” ⬇
- 3338 Failure Friday: “They just weren’t interested in what we were selling…” ⬇
- 3337 TBT: The Mushroom Kingdom of North Carolina ⬇
- 3336 Q&A: “Is there a way to trade plane tickets for profit?” ⬇
- 3335 Q&A: “What separates small earners from big ones?” ⬇
- 3334 First $1,000: “I started by setting up a booth at the farmer’s market…” ⬇
- 3333 Game of Cones: Two Women Make Architecturally-Inspired Ice Cream ⬇
- 3332 Q&A: “How to sell a reusable fork…” ⬇
- 3331 Dog Stocking Hustle Earns Husky Payoff ⬇
- 3330 TBT: The Accountant Who Sold Spreadsheets to Etsy Sellers ⬇
- 3329 Q&A: “Should I pay a publicist to book me as a podcast guest?” ⬇
- 3328 Q&A: “Why do online courses cost so much—or so little?” ⬇
- 3327 First $1,000: “I dropped off hundreds of orders at the post office…” ⬇
- 3326 Inventor Unclogs Profits With Innovative Drain Solution ⬇
- 3325 Q&A: “How can I become a personal finance influencer?” ⬇
- 3324 Failure Friday: “My virtual assistant was a fan of quiet quitting…” ⬇
- 3323 TBT: English Language Game Throws Down Amazon Gauntlet ⬇
- 3322 Q&A: “Can I import rain barrels from the Netherlands?” ⬇
- 3321 Q&A: “Should I start a new business or expand my current one?” ⬇
- 3320 First $1,000: Michigan Accountant Moonlights as Engagement Photographer ⬇
- 3319 Physician Designs Plush Toys to Teach Anatomy ⬇
January 2026 31 ep.
- 3318 Q&A: “How can I sell on a platform like NextDoor?” ⬇
- 3317 Jiu-Jitsu Instructor Pins Down Mobile Workout Tool ⬇
- 3316 TBT: Designer Scales Personalized Wedding Products to $1M+ ⬇
- 3315 Q&A: “How do I transition from Etsy to Shopify?” ⬇
- 3314 Q&A: “What’s the best software to write a non-fiction book?” ⬇
- 3313 First $1,000: “I still remember the day I hit the goal…” ⬇
- 3312 The Clothes Dryer That Changed a Family Forever ⬇
- 3311 Q&A: “Get paid to help brands with their Terms & Conditions?” ⬇
- 3310 Failure Friday: “We opened the box and it was a totally different product…” ⬇
- 3309 TBT: “MomBox” Expands to Popular Subscription Box Service ⬇
- 3308 Q&A: “What are the ethics of paid referrals to therapists?” ⬇
- 3307 Q&A: “Should I charge a flat fee or percentage?” ⬇
- 3306 First $1,000: “The pre-launch strategy produced $1,000 on day one…” ⬇
- 3305 Engineer Makes $80,000/Year Handing Out Free Maps ⬇
- 3304 Q&A: “Is it better to have more projects or a single focus?” ⬇
- 3303 Food Tour Guide Chomps Down on $100,000 Profit ⬇
- 3302 TBT: Mystery Trip Biz Doubles Down on Thrills ⬇
- 3301 Q&A: “How do songs get licensed for background music?” ⬇
- 3300 Q&A: “How many ‘wine-of-the-month’ clubs are there??” ⬇
- 3299 First $1,000: Fashion Affiliate Earns $10,000/Month ⬇
- 3298 Rehearsal App for Actors Earns $500,000 ⬇
- 3297 Q&A: “Should I pay $2,000 for a domain name I really want?” ⬇
- 3296 Failure Friday: “Apple rejected my game before it even launched…” ⬇
- 3295 TBT: Best Guitar Lessons in the Universe ⬇
- 3294 Q&A: “I’m offering executive coaching at a high price…” ⬇
- 3293 Q&A: “How can an author succeed these days?” ⬇
- 3292 First $1,000: Comedy Podcast Editor Creates Recurring Income ⬇
- 3291 Dachshund-Loving Duo Designs Doxie Apparel ⬇
- 3290 Q&A: “What if you don’t want to use social media?” ⬇
- 3289 Rent the Chicken! An Egg-Cellent Idea Clucks Into Cash ⬇
- 3288 Side Hustle School Season 10 Starts TODAY ⬇