Failure Friday Episodes
208 Failure Friday episodes are the most honest thing in the side hustle space. Real people share what didn't work -- and why. These aren't cautionary tales, they're learning machines. The side hustle that failed often became the foundation for the one that worked.
- Failure Friday: "I had to issue refunds and cancel 50 orders…"
Shopify seller cancelled 50 orders and issued refunds after accidentally bypassing inventory sync during a sales spike. Side Hustle School Ep. 3394.
- 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.
- Failure Friday: "A $300 mistake cost me $100,000"
A $300 mistake cost Joel Runyon $100,000—what went wrong and why it matters for entrepreneurs. Side Hustle School Ep. 3366.
- Failure Friday: "Our first trade show was canceled with no refund..."
Trade show investment lost when event canceled with no refund—what one Maine artisan learned. Side Hustle School Ep. #3352.
- Failure Friday: “They just weren’t interested in what we were selling…”
Wedding livestream business failed to pivot during Covid—market just wasn't interested. Side Hustle School Ep. 3338.
- Failure Friday: “My virtual assistant was a fan of quiet quitting…”
What happens when your virtual assistant practices quiet quitting and you stop paying attention. Side Hustle School Ep. 3324.
- Failure Friday: “We opened the box and it was a totally different product…”
When a supplier sent the wrong kettlebell order, the founder had to rebuild trust. Side Hustle School Ep. 3310.
- Failure Friday: “Apple rejected my game before it even launched…”
Apple rejected this mobile game developer's app before launch—and the lessons that taught them. Side Hustle School Ep. 3296.
- Failure Friday: The Multi-Platform Freelance Overload
Why expanding to Fiverr backfired for a freelance graphic designer with Upwork success—and what she learned. Side Hustle School Ep. 2918.
- Failure Friday: When My Side Hustle Took Over My Life
Side hustle success turned burnout: how a tech professional's design business overwhelmed work and life. Side Hustle School Ep. 2911.
- Failure Friday: Mobile Massage Service Gets Shut Down
Mobile massage service shut down by mall management for operating without permits. Why location matters more than you think. Side Hustle School Ep. 2904.
- Failure Friday: “Good Political News” Channel Runs Out of Stories
Why a "good political news" YouTube channel ran out of content to share. Side Hustle School Ep. 2897.
- Failure Friday: Sugar-Coated Advice Crumbles Cake Dreams
Custom cake baker's pricing mistakes and bad advice tank Charlotte business. What went wrong and why it matters. Side Hustle School Ep. 2890.
- Failure Friday: Trademark Troubles Topple New Business
How trademark issues derailed a new business in Charlotte. A cautionary tale for entrepreneurs. Side Hustle School Ep. 2883.
- Failure Friday: Overworked Freelancer Gets Stressed Out
Freelance writer takes on too many clients and burns out from poor scheduling. What went wrong and how to avoid it. Side Hustle School Ep. 2876.
- Failure Friday: The Virtual Workout Fitness Flop
A fitness coach's DIY social media strategy for virtual workouts led to costly mistakes. What went wrong and why. Side Hustle School Ep. 2869.
- Failure Friday: Stock Photo Platform Lowers Commissions
Landscape photographer's Shutterstock income tanked after commission cuts—why depending on one platform is risky. Side Hustle School Ep. 2862.
- Failure Friday: Translation Mishap Derails Import Business
A Japanese translation error tanked an import business—here's what went wrong. Side Hustle School Ep. 2855.
- Failure Friday: Why My “Alt MBA” Program Flopped
Why a college teacher's online "Alt MBA" program failed and what entrepreneurs can learn. Side Hustle School Ep. 2848.
- Failure Friday: The Corporate Gig Where I Undersold Myself
Why underpricing kills deals: a corporate speaking gig where poor negotiation cost thousands. Side Hustle School Ep. 2841.
- Failure Friday: The Challenges of Helping Smokers Switch to Vaping
Why a vaping transition business failed to attract paying clients. What went wrong and why it matters. Side Hustle School Ep. 2834.
- Failure Friday: Lessons from a Candle Subscription Box
Why a candle subscription box failed—and what pivoted to bulk restaurant sales instead. Side Hustle School Ep. 2827.
- Failure Friday: The Downside of DIY Platforms
Why a course creator's DIY platform backfired—and what went wrong. Side Hustle School Ep. 2820.
- Failure Friday: IP Complaint Ends Anime T-Shirt Venture
Anime T-shirt seller faced IP complaint and delisting. What intellectual property mistakes cost this entrepreneur. Side Hustle School Ep. 2813.
- Failure Friday: Coder’s App Flops on Product Hunt
Coder launches app on Product Hunt without market research—and learns a costly lesson. Side Hustle School Ep. 2806.
- Failure Friday: Bouncing Back After Two Years of Discouragement
Two years of discouragement didn't stop this entrepreneur—a new idea took off immediately. What changed. Side Hustle School Ep. 2799.
- Failure Friday: The Case of the Disappearing Developer
A web developer disappears mid-project, locking a business owner out during peak sales. What went wrong and lessons learned. Side Hustle School Ep. 2792.
- Failure Friday: A Year Spent Writing the Wrong Book
A programmer spent a year writing a 300-page book only to realize it was too generic. What he learned from the failure. Side Hustle School Ep. 2785.
- Failure Friday: How a $20,000 Mastermind Led Me Astray
A $20,000 mastermind group left this coach overwhelmed and lost when ecommerce advice didn't fit her business. Side Hustle School Ep. 2778.
- Failure Friday: Executive Function Coach Experiences Burnout
Executive function coach burns out from rapid growth. How scaling too fast can backfire. Side Hustle School Ep. 2771.
- Failure Friday: A Cautionary Tale of Blog Monetization
How a nomadic blogger's sustainable traffic collapsed after an algorithmic update—and what went wrong. Side Hustle School Ep. 2764.
- Failure Friday: Lost Contract Leads to 50% Revenue Drop
Employee training consultant loses 50% revenue after losing single major contract. Why diversification matters. Side Hustle School Ep. 2757.
- Failure Friday: ADHD Diagnosis Helps Frazzled Consultant
How an ADHD diagnosis helped an educational consultant overcome burnout and refocus her business. Side Hustle School Ep. 2750.
- Failure Friday: A Lego Reseller’s Lesson in Integrity
Lego reseller learns hard lesson when a deal that seemed too good to be true turned out to be. Failure Friday. Side Hustle School Ep. 2743.
- Failure Friday: The SEO Consultant’s Outsourcing Oversight
How an SEO consultant's outsourcing decision backfired—and what went wrong. Side Hustle School Ep. 2736.
- Failure Friday: Influencer’s Partner Deal Becomes Bitter Pill to Swallow
How a fitness influencer's supplement partnership backfired without proper vetting. What went wrong and why it matters. Side Hustle School Ep. 2729.
- Failure Friday: A Graphic Designer’s Brush with Copyright Catastrophe
A graphic designer's copyright mistake and what it cost her business. Side Hustle School Ep. 2722.
- Failure Friday: Vintage Watch Restorer Learns Timely Lesson
Vintage watch restorer learns hard lesson about client communication gone wrong. Side Hustle School Ep. 2715.
- Failure Friday: Fashion Forward Idea Goes Solo
Waiting on a friend to co-start a fashion blog cost six months. Why going solo matters for entrepreneurs. Side Hustle School Ep. 2708.
- Failure Friday: The Mobile App Marketplace Misfire
Mobile app marketplace referral model hits a wall: why App Store earnings proved nearly impossible. Side Hustle School Ep. 2701.
- Failure Friday: Tech Dream to Prototype Dilemma
Wearable tech entrepreneur learns hard lessons about product development costs and market reality. Side Hustle School Ep. 2694.
- Failure Friday: Debugging a Modern Business Idea
How AI made a personalized coding tutorial business obsolete. Eric from Omaha learned why staying ahead of tech matters. Side Hustle School Ep. 2687.
- Failure Friday: The Co-Working Conundrum
Why a freelancer's coworking space gamble backfired and what it reveals about solo work expectations. Side Hustle School Ep. 2680.
- Failure Friday: Bali Housing Network Falls Flat
Why a Bali short-term housing network failed against Airbnb's market dominance. What this entrepreneur learned. Side Hustle School Ep. 2673.
- Failure Friday: The Unexpected Inventory Overflow
How a women's clothing seller's holiday inventory forecast backfired—and what went wrong. Side Hustle School Ep. 2666.
- Failure Friday: AI Chatbot Goes Off the Rails
AI chatbot customer service fails spectacularly for ecommerce seller. What went wrong and why it matters. Side Hustle School Ep. 2659.
- Failure Friday: Monthlong Ad Budget Gets Spent in One Day
Kitchenware seller spends entire monthly ad budget in one day due to advertising error. Side Hustle School Ep. 2652.
- Failure Friday: Strumming Into Silence
Online guitar lessons business failed to attract beginners—in-person instruction proved irreplaceable. Side Hustle School Ep. 2645.
- Failure Friday: Useless Business Coach Fails to Help Side Hustler
Why a side hustler fired her business coach after realizing she knew her business better. Side Hustle School Ep. 2638.
- Failure Friday: Lost in the Code of Education
How an AI tutoring platform's complexity killed the business—what Colin learned from EduAI's failure. Side Hustle School Ep. 2631.
- Failure Friday: Organic Cosmetics Line Breaks Down
What went wrong with an organic cosmetics line and why product testing matters for beauty entrepreneurs. Side Hustle School Ep. 2624.
- Failure Friday: The Great Salt Lake Brewery Blunder
How a Salt Lake City brewery startup failed and what the founder learned. Side Hustle School Ep. 2617.
- Failure Friday: “I abandoned a growing email list…”
Abandoning an email list after building momentum: why consistency matters for online retailers. Side Hustle School Ep. 2610.
- Failure Friday: Lots of Followers, but Few Buyers
Why a large Instagram following didn't translate into home decor sales for one creator. Side Hustle School Ep. 2603.
- Failure Friday: “I got banned on LinkedIn!”
LinkedIn coach's aggressive marketing tactics led to account ban—a costly lesson about platform rules. Side Hustle School Ep. 2596.
- Failure Friday: Corporate Board Game Idea Fizzles Out
What went wrong when a corporate trainer tried selling custom board games for company retreats. Side Hustle School Ep. 2589.
- Failure Friday: The Fitness App Fumble
Why a personal trainer's fitness app failed to capture the energy of in-person classes. Side Hustle School Ep. 2582.
- Failure Friday: Historic Ambitions, Modern Missteps
A couple's boutique hotel dream derailed by renovation costs and lost earnest money. What they learned. Side Hustle School Ep. 2575.
- Failure Friday: The Romance Writing Reality Check
Romance author learns self-publishing isn't easy: editing and audiobook production reveal the real work behind Kindle Direct Side Hustle School Ep. 2568.
- Failure Friday: The AI Assistant That Arrived Too Early
Why an AI assistant app failed before the market was ready. Cameron Hayes shares what went wrong and why timing matters. Side Hustle School Ep. 2561.
- 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.
- Failure Friday: Follower Fallout from Buying Instagram Bots
Why buying Instagram bots backfired for a lifestyle blogger's engagement. Failure Friday lesson on growth shortcuts. Side Hustle School Ep. 2547.
- Failure Friday: Profitable Affiliate Website Peters Out
How an affiliate marketer's success mindset became his biggest liability. A cautionary tale about ignoring warning signs. Side Hustle School Ep. 2540.
- Failure Friday: Working Remotely from Thailand Is Stressful!
Software engineer's Thailand move backfires: midnight work hours prove unsustainable. Failure Friday on remote work pitfalls. Side Hustle School Ep. 2533.
- Failure Friday: He Bought a ‘Bored Ape’ NFT for $80,000
NFT investor paid $80,000 for a Bored Ape and watched it drop 40% in value—a cautionary tale about speculative assets. Side Hustle School Ep. 2526.
- 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.
- Failure Friday: PayPal Freezes $50,000 in Ticket Fees
Event host loses $50,000 in ticket sales when PayPal freezes account—what went wrong and why it matters for entrepreneurs. Side Hustle School Ep. 2512.
- Failure Friday: “Remote Year” Nomad Experiences Blogger Burnout
Digital nomad blogger struggles with burnout while traveling full-time and building a business on the road. Side Hustle School Ep. 2505.
- Failure Friday: The Handmade Hustle Hassle
How a handmade jewelry maker's cost-cutting shortcuts after sudden sales success cost her customer trust. Side Hustle School Ep. 2498.
- Failure Friday: Gourmet Chef Gets Lost in the Sauce
Philadelphia chef's gourmet food truck strategy backfired—here's what went wrong and why it matters. Side Hustle School Ep. 2491.
- Failure Friday: The Autumn Sweater Stockpile Saga
Retailer Sarah bet half her startup capital on holiday sweaters—and watched profits vanish when inventory didn't sell. Side Hustle School Ep. 2484.
- Failure Friday: Running a PR Agency Is Harder Than It Looks
Why a PR agency startup failed and what communications grads overlook. Failure Friday reveals costly lessons. Side Hustle School Ep. 2477.
- Failure Friday: Turns Out Ideas Don’t Magically Happen
Why ideas stay stuck without action—and how to break the pattern. Side Hustle School Ep. 2470.
- Failure Friday: Halloween Festival Gets Rained Out
A grade-school teacher's fall festival side hustle faces more than just bad weather. What went wrong and why it matters. Side Hustle School Ep. 2463.
- Failure Friday: “We didn’t realize every order was free…”
Restaurant owner's DoorDash setup error costs $1,500 in free orders—a cautionary tale for platform integration. Side Hustle School Ep. 2456.
- Failure Friday: Chicago Coffee Roaster Grinds to Halt
Chicago coffee roaster's side hustle fails—and what it teaches about scaling too fast. Side Hustle School Ep. 2449.
- Failure Friday: Graveyard Yoga Fails to Entice Living or Dead
Yoga instructor launches Graveyard Yoga series with zero sign-ups. Why niche concepts don't always resonate. Side Hustle School Ep. 2442.
- Failure Friday: The Destination Yoga Retreat That Wasn’t
Yoga teacher's Central America retreat idea failed before it started—here's why no one signed up. Side Hustle School Ep. 2435.
- Failure Friday: Don’t Forget to Renew Your Domain Names!
How a personal finance blogger lost his domain name to a competitor—and why auto-renewal matters for your business. Side Hustle School Ep. 2428.
- Failure Friday: Bank Cancels TikTok Star’s Revenue Stream
TikTok streamer loses income when banking partner drops her from affiliate program. What went wrong and why it matters. Side Hustle School Ep. 2421.
- Failure Friday: Couples’ Intimacy Coach Fails to Spark Passion
Why a couples' intimacy coaching side hustle crashed before takeoff. What Julia learned from the failure. Side Hustle School Ep. 2414.
- Failure Friday: “Once I knew I had ADHD, everything made more sense…”
How ADHD diagnosis transformed a programmer's struggle with procrastination and motivation. Side Hustle School Ep. 2407.
- Failure Friday: The Dial-a-Poem Hotline
Why a poetry hotline failed to turn profit despite being creative. Side Hustle School Ep. 2400.
- Failure Friday: Ghost Tours Fail to Scare Enough Clients
Why a Denver ghost tour business failed to attract enough customers. What went wrong and lessons for entrepreneurs. Side Hustle School Ep. 2393.
- Failure Friday: Homemade Hummus Subscription Fails to Smash
Homemade hummus subscription box fails to gain traction. Why this Lebanese-inspired side hustle couldn't scale. Side Hustle School Ep. 2386.
- Failure Friday: “SnoozeCubes” Hustle Experiences Sleepy Sales
Why office nap pods failed despite early hype—a cautionary tale from the founder. Side Hustle School Ep. 2379.
- Failure Friday: “Hangover Helper” Business Sobers Up
Why a San Francisco "Hangover Helper" startup wilted during the 2020 pandemic. Side Hustle School Ep. 2372.
- Failure Friday: On-Demand Haiku Poet Shows Restraint
On-demand haiku poet earns $75,000 before realizing the business model doesn't work. What Riley learned about bad ideas. Side Hustle School Ep. 2365.
- Failure Friday: Professional Line-Stander Sits Down
Professional line-stander business idea fails to gain traction. Why this niche service couldn't attract paying customers. Side Hustle School Ep. 2358.
- Failure Friday: Fortune Cookie Writer Fails to Foresee Profit
Why a fortune cookie writing side hustle crumbled before it could profit. Side Hustle School Ep. 2351.
- Failure Friday: “Fake Wedding Guest” Biz Fizzles Out
Why a "fake wedding guest" service failed—and what entrepreneurs can learn from it. Side Hustle School Ep. 2344.
- Failure Friday: Rent-a-Friend Fails to Launch in Tulsa
Rent-a-Friend business model fails in Tulsa, Oklahoma. What went wrong when a side hustler tried importing a Japanese idea. Side Hustle School Ep. 2337.
- Failure Friday: Chicken Rental Service Fails to Egg-cite
Why a Boise chicken rental business failed to take flight. Learning from side hustle mistakes. Side Hustle School Ep. 2330.
- Failure Friday: “Looking back on my picnic misadventures…”
Why a Miami caterer's customized picnic lunch idea flopped and what it teaches entrepreneurs. Side Hustle School Ep. 2323.
- Failure Friday: “Puzzlemaster of Cleveland” Fails to Break Even
City engineer's corporate puzzle night side hustle fails to break even. What went wrong and why it matters for entrepreneurs. Side Hustle School Ep. 2316.
- Failure Friday: “Ultimate Wrinkle Inducer” MLM Flops
How an office manager got trapped in a makeup MLM and why it failed. What she learned about avoiding schemes. Side Hustle School Ep. 2309.
- Failure Friday: Airbnb Is Harder Than It Looks
NYC Airbnb rental rules derail side hustle attempt—why short-term rental restrictions matter for entrepreneurs. Side Hustle School Ep. 2302.
- Failure Friday: Flip Phone Reselling Fails to Cell Phones
Flip phone reselling in San Diego backfired when a hustler couldn't sell a single device. What went wrong and why. Side Hustle School Ep. 2295.
- Failure Friday: “I tried wearing lettuce on my head to get attention…”
What went wrong when a fashion blogger tried wearing lettuce on her head to go viral. Side Hustle School Ep. 2288.
- Failure Friday: Minimalism Expert Becomes Disillusioned
How a minimalism expert became uncomfortable with commercializing the philosophy. Failure Friday on Side Hustle School Ep. 2281.