Failure Friday Episodes
- Failure Friday: “My first client was a total nightmare…”
How a personal shopper's difficult first client nearly derailed her business before it started. Side Hustle School Ep. 2274.
- Failure Friday: The “American Ninja Warrior” Personal Trainer
Personal trainer's "American Ninja Warrior" specialization backfired in Tacoma—what went wrong and why. Side Hustle School Ep. 2267.
- Failure Friday: The Influencer Who Quit Instagram
Why an Instagram influencer strategy failed and what it taught about platform dependency. Side Hustle School Ep. 2260.
- 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.
- Failure Friday: “My business was like a coupon, it expired too soon…”
Why a coupon directory business expired fast: Jan spent more than she saved. Side Hustle School Ep. 2246.
- Failure Friday: “I wasn’t making enough money to cover expenses…”
Travel agent side hustle failed when a bulk booking was cancelled, leaving expenses uncovered. Side Hustle School Ep. 2239.
- Failure Friday: Bunny Breeding Gone Bad
Rabbit breeding startup fails spectacularly in Las Vegas. What went wrong and why it matters for aspiring entrepreneurs. Side Hustle School Ep. 2232.
- Failure Friday: “The scavenger hunt turned into a rainstorm…”
What went wrong when a scavenger hunt side hustle hit a rainstorm during a major client event. Side Hustle School Ep. 2225.
- Failure Friday: “I held a sock puppet show while processing transactions…”
Sock seller's credit card processor fails at trade show, forcing improvisation. What went wrong and why it matters. Side Hustle School Ep. 2218.
- Failure Friday: “The client was shocked by the amount of taxes they owed…”
Bookkeeper overstates client income on tax return, creating costly consequences. What went wrong and why it matters. Side Hustle School Ep. 2211.
- Failure Friday: “I had to reel in my losses and start from scratch…”
A fisherman's fishing shop fails when big box retailers move to town. What went wrong and why it matters. Side Hustle School Ep. 2204.
- Failure Friday: “On the day of the wedding, a huge storm rolled in…”
Wedding planner learns harsh lesson when storm hits ceremony in Hermosa Beach. What went wrong and why it matters. Side Hustle School Ep. 2197.
- Failure Friday: “I think I had some unrealistic expectations…”
NFT artist spent 3 months creating 5,000 digital works but sold only 10% before abandoning the project. Failure Friday on Side Hustle School Ep. 2190.
- Failure Friday: “The sleigh kept getting bogged down…”
What went wrong when a North Pole entrepreneur's sleigh business faced early obstacles. Failure Friday story. Side Hustle School Ep. 2183.
- Failure Friday: “No one wanted my idea, even for free…”
What went wrong when a personal trainer launched a virtual shoe-fitting service with zero traction. Side Hustle School Ep. 2176.
- Failure Friday: “My virtual assistant was a fan of quiet quitting…”
What went wrong when an advisory service founder hired his first virtual assistant without staying involved. Side Hustle School Ep. 2169.
- Failure Friday: “My maple syrup was stolen by a Canadian cartel…”
Maple syrup reseller loses inventory to Canadian cartel—a sticky failure with surprising lessons. Side Hustle School Ep. 2162.
- Failure Friday: “I never should have borrowed money to invest…”
Borrowing money to invest in cryptocurrency without due diligence—and why it matters for entrepreneurs. Side Hustle School Ep. 2155.
- Failure Friday: “I invested in a franchise and now I feel stuck…”
Franchise investment left him feeling trapped with a job, not a business. What Mike learned about franchise ownership. Side Hustle School Ep. 2148.
- Failure Friday: “I wish I hadn’t told my friends about my hustle…”
How telling friends about your side hustle backfired for a tech employee. What went wrong and why it matters. Side Hustle School Ep. 2141.
- Failure Friday: “My Facebook page with 40,000 fans was hacked…”
Coach lost 40,000 Facebook fans to hacker—and her six-figure business. What went wrong and why it matters. Side Hustle School Ep. 2134.
- Failure Friday: “Apple rejected my game before it even launched…”
Apple Store rejection killed this indie mobile game before launch. What Matt learned from failure. Side Hustle School Ep. 2127.
- Failure Friday: “My anniversary sale was an epic fail…”
How a six-figure membership site founder lost momentum by neglecting what made it successful. Side Hustle School Ep. 2120.
- Failure Friday: “I got sucked into hosting an MLM party…”
Why MLM parties fail: one entrepreneur learns the hard way that network marketing events alienate friends. Side Hustle School Ep. 2113.
- Failure Friday: “I tried to sell something no one wanted…”
What went wrong when a seller tried to launch gift baskets for college alumni with no market research. Side Hustle School Ep. 2106.
- Failure Friday: “I had tears in my eyes reading the response…”
How a jewelry seller nearly lost her six-figure business to one negative review. Failure Friday on Side Hustle School Ep. 2099.
- Failure Friday: “I had to issue refunds and cancel 50 orders…”
How a Shopify party favor seller issued refunds on 50 orders after a single inventory panel mistake. Side Hustle School Ep. 2092.
- Failure Friday: “My boss discovered my side hustle by accident…”
Employee's side hustle exposed when boss finds website code on unattended desktop. A six-figure mistake. Side Hustle School Ep. 2085.
- Failure Friday: “It should have been a small mistake…”
Organic cosmetics brand owner's product launch disaster and what went wrong. A small mistake that wasn't so small. Side Hustle School Ep. 2078.
- Failure Friday: “I thought I’d set up the website incorrectly…”
A middle-school principal's volleyball blog fails to gain traction. What went wrong and why it matters for side hustlers. Side Hustle School Ep. 2071.
- Failure Friday: “This is super embarrassing looking back…”
Atlanta stationary designer's Amazon gamble cost her six figures. Lucky Dog Design's costly mistake. Side Hustle School Ep. 2064.
- Failure Friday: “Then one afternoon I got a call from the police…”
Electric vehicle rental startup collapse: what went wrong and why police got involved. Side Hustle School Ep. 2057.
- Failure Friday: “Kickstarter rejected my project right before launch…”
Kickstarter rejected Bad Day Box's snail mail self-care launch at the last minute—here's what went wrong and what saved it. Side Hustle School Ep. 2050.
- Failure Friday: “After I was hit by a car, things got worse…”
Car accident derailed affiliate marketer's $2,500/month business. What went wrong and why it matters. Side Hustle School Ep. 2043.
- Failure Friday: “Despite my best efforts, no one was buying…”
Writing coach's Facebook ads failure: spent money before product-market fit. Why timing matters for paid marketing. Side Hustle School Ep. 2036.
- Failure Friday: “We had no desire to help college students cheat…”
How a naming mistake almost derailed an animation startup—and what the co-founder learned. Side Hustle School Ep. 2029.
- Failure Friday: “We opened the box and it was a totally different product…”
What went wrong when a kettlebell supplier sent the wrong product to a new ecommerce business. Side Hustle School Ep. 2022.
- Failure Friday: “Amazon permanently banned my seller account…”
How a six-figure Amazon reseller got permanently banned over a supplier problem. What went wrong and why it matters. Side Hustle School Ep. 2015.
- Failure Friday: “The experience of hearing rejection was important…”
Facing manufacturer rejection while building KindRoot plant-powered lozenges. How she learned to trust herself. Side Hustle School Ep. 2008.
- Failure Friday: “Don’t let customers pay after services have been rendered…”
Credit card chargebacks hit tutoring businesses hard—here's why payment timing matters. Side Hustle School Ep. 2001.
- Failure Friday: “We tried to be everything to everyone…”
Parking lot cleanup founder earned $20K/month by refocusing on core service after overexpanding. Failure Friday. Side Hustle School Ep. 1994.
- Failure Friday: “I acted like an inexperienced order-taker…”
Freelance writer Alli Hill learns why order-taking mentality cost clients—and how communication built her six-figure business. Side Hustle School Ep. 1987.
- Failure Friday: “We locked ourselves in a room for six months to build…”
Sportsbookr co-founder locked in a room for six months building—then learned validation isn't one-time. What went wrong. Side Hustle School Ep. 1980.
- Failure Friday: “Offensive Greeting Cards” Lost in Post
UK greeting card business lost $36,000/month shipment to overseas supplier mishap. A costly lesson in supply chain management. Side Hustle School Ep. 1973.
- Failure Friday: “80% of our customers never returned…”
How a six-figure baseball subscription box nearly collapsed after a website migration disaster. Side Hustle School Ep. 1966.
- Failure Friday: “Switchasaurus” Card Game Almost Goes Extinct
Switchasaurus card game maker earns $64,000 but faces manufacturing crisis. Supplier underdelivers, threatening extinction. Side Hustle School Ep. 1959.
- Failure Friday: “I naively thought the influencers would bring sales…”
Influencer marketing flop: Australian ecommerce founder wastes budget on Instagram promotions that deliver no sales. Side Hustle School Ep. 1952.
- Failure Friday: “They just weren’t interested in what we were selling…”
Why a livestream wedding business's pivot failed when they assumed other markets wanted their service. Side Hustle School Ep. 1945.
- Failure Friday: “My app kept crashing during the big pitch…”
App crashed during investor pitch for iGoal project management tool earning $2,000/month. What went wrong and why it matters. Side Hustle School Ep. 1938.
- Failure Friday: “I walked away at the last minute…”
When a municipal composting contract seemed promising, the founder of Wastewell had to walk away. A cautionary tale. Side Hustle School Ep. 1931.
- Failure Friday: “I’ve never talked openly about what I’m working on…”
Recipe site founder earns $1,000/month with ad-free platform, but struggled to share her idea after a previous project failed. Side Hustle School Ep. 1924.
- Failure Friday: “They said it was a wonderful opportunity…”
Private chef gave free meals to Instagram influencers—and earned nothing. What Chris Spear learned about marketing mistakes. Side Hustle School Ep. 1917.
- Failure Friday: “My first customer bought out of pity…”
How a reusable cutlery seller overcame early market rejection and imposter syndrome to build $2,000/month business. Side Hustle School Ep. 1910.
- Failure Friday: “The reality was not as awesome as the dream…”
What went wrong when a couple launched their vintage camper rental business—and why details matter more than dreams. Side Hustle School Ep. 1903.
- Failure Friday: “If I want to do good work, I can’t sacrifice my wellbeing…”
Card game creator learns she can't build her business while sacrificing her wellbeing. A Failure Friday story. Side Hustle School Ep. 1896.
- Failure Friday: “Something miraculous happened: I started making money…”
Birthday Buddy founder's free app failed, but the paid version now makes $2,000/month. How a mistake became the breakthrough. Side Hustle School Ep. 1889.
- Failure Friday: “I dropped out of Stanford and left my business at the same time…”
Dropped out of Stanford while running a vegan banana ice cream business from his dorm. What went wrong and why it matters. Side Hustle School Ep. 1882.
- Failure Friday: “I started to realize how little I knew…”
Furniture reseller takes on an ambitious project and learns a hard lesson about knowing her limits. Side Hustle School Ep. 1875.
- Failure Friday: “What you didn’t hear was how unfocused I was…”
How unfocused side hustles collapse: a 3D printed cookie cutter business owner's cautionary tale. Side Hustle School Ep. 1868.
- Failure Friday: “My Facebook page with 150,000 fans was taken over by hackers…”
Facebook page with 150,000 fans hacked: how a $700/month tailgating blogger lost control and fought to reclaim it. Side Hustle School Ep. 1861.
- Failure Friday: “If I had done any research, I would have picked a different country…”
Why skipping research cost an Australian designer $8,000/month in lost potential. Failure Friday on doing your homework. Side Hustle School Ep. 1854.
- Failure Friday: “If I could do it over again, I’m not sure I would…”
What went wrong when a British expat invested $40,000 in a bike transport business in Central America. Failure Friday on Side Hustle School Ep. 1847.
- Failure Friday: “We spent countless hours making videos no one watched…”
Why Master ABA's founders wasted months on unwanted videos—and what they learned. Side Hustle School Ep. 1840.
- Failure Friday: “My complacency set in over time…”
How a six-figure men's fashion site lost momentum through complacency—and what the founder learned. Side Hustle School Ep. 1833.
- Failure Friday: Self-Guided London Food Tours Fail to Excite
Why a self-guided London food tour startup failed despite parent business success. Side Hustle School Ep. 1826.
- Failure Friday: “I had to take a hard look at my business model…”
When Facebook ads stop working, a $50,000/year vintage radio restoration business faces a crisis. What went wrong and why. Side Hustle School Ep. 1819.
- Failure Friday: “We went all-in on applying for a $2 million grant…”
What happened when Generation Mindful went all-in on a $2M NIH grant—and what they learned from rejection. Side Hustle School Ep. 1812.
- Failure Friday: “All I had to do was hit the record button…”
What went wrong when an online cooking club host forgot to hit record during a 200+ member Zoom call. Side Hustle School Ep. 1805.
- Failure Friday: “Our first trade show was canceled with no refund…”
Trade show cancellation and pandemic pivot: how a Maine craftsman adapted when his first wholesale show fell through. Side Hustle School Ep. 1798.
- Failure Friday: “Perfect SAT Score” Tutor Gets Rejected by 100 Publishers
Perfect SAT score couldn't land a book deal: 100+ publisher rejections. What Prep Expert founder learned from failure. Side Hustle School Ep. 1791.
- Failure Friday: “Weeks after launch, the website was totally dead…”
How a roommate finder website nearly died before becoming a global success. What Rupert Hunt learned about commitment. Side Hustle School Ep. 1784.
- Failure Friday: “No one wanted a bat house during the pandemic…”
Bat house sales crashed during the pandemic—here's what went wrong and why. Side Hustle School Ep. #1777.
- Failure Friday: “We hired a designer who said she could do everything…”
Hiring a designer who promised everything went wrong for TuckTats co-founders. What they learned about vetting contractors. Side Hustle School Ep. 1770.
- Failure Friday: “We failed to account for the ingredients to success…”
How a Nashville handmade goods business lost $300k expanding too fast. Pride before the fall. Side Hustle School Ep. 1763.
- Failure Friday: Live Theater Rebrand Meets Global Pandemic
Theater captioning app faced pandemic shutdown after ambitious 2020 rebrand. Matthew Bivens on what went wrong. Side Hustle School Ep. 1756.
- Failure Friday: “I was exhausted and doing the bare minimum for my business…”
How burnout nearly killed an adventure brand owner's side hustle while traveling. What she learned about doing less. Side Hustle School Ep. 1749.
- Failure Friday: Supplier Problem Harms Client Relationship
Cork sunglasses supplier delay broke client relationship—what went wrong. Joseph O'Bell's $100k lesson. Side Hustle School Ep. 1742.
- Failure Friday: Pancake Art in Bangkok Fails to Flip
Pancake art startup Dancakes faced disaster expanding to Bangkok—here's what went wrong. Side Hustle School Ep. 1735.
- Failure Friday: “Everyone in the room said ‘Turn it off!’…”
Yoga studio founder's VIP event derailed when the sound system failed mid-experience. Side Hustle School Ep. 1728.
- Failure Friday: “A bad hire will set you back six months…”
Bad hire setbacks: Davis Nguyen's $90K/month consulting firm lost months to a poorly-vetted virtual assistant. Side Hustle School Ep. 1721.
- Failure Friday: Dating Profile Ghostwriter Struggles to Launch App
What went wrong when a dating app founder tried to launch with online ads. A Failure Friday story. Side Hustle School Ep. 1714.
- Failure Friday: “Hundreds of people were shut out of my webinar…”
Boudoir photographer's webinar platform crashed with 400 attendees but only 50 capacity. What went wrong and why it matters. Side Hustle School Ep. 1707.
- Failure Friday: “I didn’t know my business partner was a convicted felon…”
Business partner's hidden criminal past threatens seven-figure drone training company. Side Hustle School Ep. 1700.
- Failure Friday: “We made a ton of investment … then we decided to close.”
Escape room founder invested heavily in San Francisco expansion, then shut it down. What went wrong and why. Side Hustle School Ep. 1693.
- Failure Friday: Ice Glass Event Business Melts Down
Ice mug business melts down at outdoor event on unseasonably warm Minnesota day. What went wrong and why it matters. Side Hustle School Ep. 1686.
- Failure Friday: “I realized really quickly that no one was buying…”
Why Amy McCord Jones' flower business almost failed without product photography. Skipping photos cost her sales. Side Hustle School Ep. 1679.
- Failure Friday: Weighted Blankets Get Weighed Down in Customs
Weighted blanket business hits customs disaster during peak season, costing six figures. What went wrong and why it matters. Side Hustle School Ep. 1672.
- Failure Friday: Tea Supply Chain Meets Its Matcha
When a tea supplier's supply chain crumbles during the pandemic, Luciana Torous learns hard lessons about business resilience. Side Hustle School Ep. 1665.
- Failure Friday: “They refused to listen to my big pitch…”
Product inventor hits legal wall pitching peeLUX shapewear accessory to Spanx founder. What went wrong. Side Hustle School Ep. 1658.
- Failure Friday: “They promised the boat would be ready… but it wasn’t.”
When a Mediterranean cruise operator commissioned a custom ship, the builder missed deadlines and nearly sank the business. Side Hustle School Ep. 1651.
- Failure Friday: Antiracism Interest Grows, But What Do Clients Want?
Workplace inclusion agency grew fast, but clients had misaligned goals and unclear needs. What went wrong and why it matters. Side Hustle School Ep. 1644.
- Failure Friday: “It took me way too long to bounce back…”
Personal finance blogger launches coaching program, gets zero response, takes two years to recover. Key lessons from failure. Side Hustle School Ep. 1637.
- Failure Friday: “Pitching to executives felt like an awful first date…”
Greeting card entrepreneur unprepared for executive pitch at incubator. Failure Friday on winging it. Side Hustle School Ep. 1630.
- Failure Friday: “At 3am in the Emergency Room, I realized I should take better care of myself…”
Overworking yourself to burnout: why a sustainable design founder ended up in the ER at 3am. Side Hustle School Ep. 1623.
- Failure Friday: “The client ordered the most expensive thing on the menu…”
What went wrong when a client ordered the most expensive thing on the menu—and why contract limits matter for side hustlers. Side Hustle School Ep. 1616.
- Failure Friday: “My D.C. tour business was down 89%…”
D.C. tour guide's business drops 89% during COVID-19 pandemic. What went wrong and why it matters for side hustlers. Side Hustle School Ep. 1609.
- Failure Friday: “I thought I had the Midas touch…”
Digital marketer with a $50,000/month business launches a "killer app" that fails. What went wrong and why. Side Hustle School Ep. 1602.
- Failure Friday: “If it worked once, it should work twice… right?”
Parenting blogger earned $2,000/month blogging, then assumed his YouTube strategy would work the same way. It didn't. Side Hustle School Ep. 1595.
- Failure Friday: Manufacturing in China—How Hard Can It Be??
Manufacturing outsourcing to China backfired for a six-figure wellness planner brand. What went wrong and why it matters. Side Hustle School Ep. 1588.
- 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.