Events & Entertainment Side Hustles
93 episodes feature people who built income around events and entertainment — DJs, entertainers, event planners, escape room operators, experience designers, and more. Events are inherently local and often underserved, which creates opportunity for people willing to show up in person.
- TBT: The Tennessee Bachelorette Party Boom
Bachelorette party planning in Nashville. Cassidy built an all-inclusive events business in America's top party destination. Side Hustle School Ep. 3351.
- 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.
- TBT: Designer Scales Personalized Wedding Products to $1M+
Graphic designer scales personalized wedding illustrations to $1M+. Custom designs for events became a seven-figure business. Side Hustle School Ep. 3316.
- 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.
- Weekend Workshop: From Wedding Dresses to State Legislature
Wedding dress entrepreneur builds path to Nebraska State Legislature. Weekend Workshop step-by-step guide for 2025. Side Hustle School Ep. 3284.
- Weekend Workshop: From Utah Piano Teacher to Digital Nomad
Utah piano teacher builds $360,000/year online music school as digital nomad. Weekend Workshop kickoff. Side Hustle School Ep. 3200.
- First $1,000: Houston Homeowner Turns Studio Into Weekend Venue
Houston homeowner transforms backyard shed into rentable photo studio and workshop space. How she hit her first $1,000. Side Hustle School Ep. 3173.
- First $1,000: Musician Creates Loop Packs for Video Editors
Musician sells loop packs to video editors, earning first $1,000 with twelve audio loops and community posts. Side Hustle School Ep. 3124.
- TBT: Lawn Sign Biz Expands to Wedding Décor Rentals
Teacher's lawn sign business pivots to wedding décor rentals. Side Hustle School Ep. 3050.
- First $1,000: Miami Divorce Planner Offers “Freedom Celebrations”
Former wedding planner in Miami pivots to organizing "freedom celebrations" for newly divorced clients. Side Hustle School Ep. 3019.
- First $1,000: Temporary Tattoo Artist for Events
Custom temporary tattoo artist for events earns first $1,000 with weddings and corporate gigs. Side Hustle School Ep. 2956.
- TBT: Austin Event Planner Goes Hard for SXSW
Austin event planner specializes in tech events during SXSW festival. How they've grown since first featured. Side Hustle School Ep. 2840.
- Q&A: “I lead tours in Scotland … but I want to expand.”
How an Edinburgh tour guide can expand beyond in-person tours into digital storytelling and passive income. Side Hustle School Ep. 2698.
- TBT: Wordsmith Officiant Elevates Wedding Rituals
Wedding officiant personalizes ceremonies and crafts memorable stories as a thriving side hustle. Side Hustle School Ep. 2686.
- Q&A: “How do I launch a successful educational podcast for kids?”
How to launch an educational podcast for kids that reaches parents and educators. Side Hustle School Ep. 2663.
- Q&A: “Should I make a tour guide app?”
Should you build a tour guide app? Validation and next steps for connecting travelers with local guides. Side Hustle School Ep. 2586.
- TBT: The Tennessee Bachelorette Party Boom
Nashville bachelorette party business thrives in fastest-growing U.S. city for events. Where is the founder now? Side Hustle School Ep. 2553.
- 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.
- Q&A: “An at-home escape room kit…”
At-home escape room kits: how a chemical engineer can validate the market and transition from a corporate job. Side Hustle School Ep. 2408.
- TBT: Hand Lettered Wedding Invites Are Here to Stay
Hand-lettered wedding invitations with custom calligraphy. A retail associate's thriving side hustle and where they are now. Side Hustle School Ep. 2399.
- 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.
- TBT: Vancouver Bike Tours Takes Scenic Route
Cycling tour business in Vancouver serves visitors and locals. How the business evolved since we first featured it. Side Hustle School Ep. 2343.
- First $1,000: City Government Staffer Leads Virtual Events
How Victoria earned her first $1,000 planning virtual weddings, networking events, and gender reveals. Side Hustle School Ep. 2298.
- TBT: Destination Wedding Officiant Travels Worldwide
Destination wedding officiant travels worldwide to officiate ceremonies in exotic locales. Where is she now? Side Hustle School Ep. 2273.
- First $1,000: Spotify Musician Gets Paid for Yoga Streams
Independent musician earns passive income from Spotify with yoga-focused playlists. How she reached her first $1,000. Side Hustle School Ep. 2256.
- 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.
- First $1,000: “I earn £2,500 per month leading London walking tours…”
London walking tour guide earns £2,500 ($3,000) monthly leading weekend tours. How Ben reached his first $1,000. Side Hustle School Ep. 2214.
- TBT: “Teaching pole dancing has been incredibly rewarding…”
Pole dance instructor builds thriving fitness business in Florida. Her students keep coming back for more. Side Hustle School Ep. 2203.
- 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.
- Q&A: “Are there any alternatives to Patreon?”
Patreon alternatives for independent musicians: Substack, Ko-fi, and direct payment options. Side Hustle School Ep. 2146.
- Q&A: “I stopped delivering for my Patreon…”
Patreon musician earned $2,000/month from fans but stopped delivering promised updates. Should he come clean or keep quiet? Side Hustle School Ep. 2132.
- First $1,000: “It came from patience and vision boarding…”
Wedding marketer Nina Addeo earned her first $1,000 with vision boarding and patience. How she built I Do Wedding Marketing. Side Hustle School Ep. 2053.
- First $1,000: “My music was played on a Romanian TV show…”
Lawyer earned his first $1,000 licensing music to Romanian TV show. How stock music became $400/month side hustle. Side Hustle School Ep. 2004.
- 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.
- Las Vegas Wedding Officiant Bets on Red
How a car rental executive became a Las Vegas wedding officiant earning six figures. Side Hustle School Ep. 1914.
- Q&A: Will this “all you can craft” event venue subscription work?
Can a subscription model save a struggling arts space? Evaluating the "all you can craft" venue idea. Side Hustle School Ep. 1898.
- Q&A: Can I market myself as a festival concierge?
Festival concierge services for VIPs: Can you market event expertise like a premium travel agent? Side Hustle School Ep. 1891.
- Q&A: “I’m building the world’s most difficult scavenger hunt…”
Building a multi-city scavenger hunt with extreme challenges—meet celebrities, swim rivers, find summer Christmas trees. Side Hustle School Ep. 1869.
- Q&A: How can my tour business earn recurring revenue?
How can tour operators shift from one-time bookings to recurring revenue? Strategies for sustainable income. Side Hustle School Ep. 1863.
- Q&A: “Square refunded my customer’s payment!”
Handling chargebacks on tour guide services: what to do when a payment processor refunds your customer without warning. Side Hustle School Ep. 1848.
- Q&A: How do songs get licensed for background music?
How independent musicians can earn more licensing music for retail stores than streaming on Spotify. Side Hustle School Ep. 1845.
- Q&A: “I’d like to be a medical claims adjustor, but for weddings”
Wedding vendor negotiation service: can you apply medical claims adjusting to weddings? Side Hustle School Ep. 1701.
- 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.
- Seattle Couple Creates New “Income LiveStream”
Wedding live streaming service fills pandemic gap for engaged couples unable to gather in person. Side Hustle School Ep. 1669.
- 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.
- Origami-Loving Musician Doesn’t Mind Paperwork
Virtual origami lessons help a New Zealand musician pay bills after pandemic cancels her tours. Side Hustle School Ep. 1548.
- Family Trio Makes Marvelous Mask Magnets
Family creates magnetic mask charms during pandemic lockdown. Influencer marketing strategy drives sales. Side Hustle School Ep. 1466.
- TBT: Florist Offers Nationwide, DIY Wedding Flowers
Wedding florist Amy McCord Jones quadrupled her DIY flower business across the US. Shipping challenges didn't stop her growth. Side Hustle School Ep. 1384.
- TBT: Teaching the World to Play Saxophone
Australian musician earns $40,000/year teaching saxophone online to global students from Melbourne. Side Hustle School Ep. 1356.
- Q&A: How can I use Spotify as a lead generation source?
How independent musicians can generate leads from Spotify and Soundcloud—and why the answer might surprise you. Side Hustle School Ep. 1350.
- Social Media Fan Ties the Knot with Wedding Marketing
How a social media expert earns $30/month with wedding marketing. Nina combines her skills with her passion for weddings. Side Hustle School Ep. 1289.
- TBT: Designer Scales Personalized Wedding Products to $1M+
Graphic designer scales personalized wedding illustrations to $1M+. Kristin Berry's custom e-commerce business in NYC. Side Hustle School Ep. 1174.
- TBT: Epic Scavenger Hunt Becomes 6-Figure Income
How Chris turned childhood scavenger hunt passion into $3,000/month across Boston, Chicago, Northeast. Side Hustle School Ep. 1132.
- Q&A: How to go from prototype into manufactured product?
How to turn a prototype into manufactured product: non-screen kids' entertainment kits generating $100,000 in sales. Side Hustle School Ep. 1114.
- TBT: Jazz Musician Becomes High Earner
Jazz musician grows hobby blog into six-figure online education business. Side Hustle School Ep. 1111.
- Atlanta Lawyer Walks Into Food Tour Biz
How an Atlanta lawyer built a six-figure food walking tour business. Scaled from passion for storytelling. Side Hustle School Ep. 990.
- Reddit Secret Santa Delivers Sack Full Of Adventure
Reddit Secret Santa gift exchange becomes a side business through creative scavenger hunts. Side Hustle School Ep. 943.
- The Great Escape! Video Game Maker Creates Real-Life Puzzle Rooms
Real-life escape rooms born from a video game designer's passion—the first American escape room company. Side Hustle School Ep. 927.
- Designer Performs Magic, Turns Dream Into Reality
Graphic designer becomes resident magician at a local bar, performing card tricks and illusions nightly. Side Hustle School Ep. 886.
- Second Grade Teacher Earns Second Income
Elementary school teacher launches wedding planning business using organizational skills. Side Hustle School Ep. 880.
- Wedding Planner Earns Passive Income with DIY Flowers
Wedding planner earns $900/month selling DIY wedding bouquets at wholesale prices. Affordable flowers for couples on a budget. Side Hustle School Ep. 863.
- Savvy Bride Turns Budget Wedding Into Six Figure Success
How a budget bride turned wedding planning into a six-figure blog. The Budget Savvy Bride generates over $100K yearly. Side Hustle School Ep. 849.
- Ad Agency Rep Designs Wedding Stationery
Wedding stationery design for Nebraska ad agency employee. Built portfolio designing invitations for friends and family. Side Hustle School Ep. 791.
- Artistic Wedding Backdrop Offers Updated Photo Alternative
Wedding backdrop rental with artistic light displays. Two friends create nontraditional photo alternatives for couples. Side Hustle School Ep. 773.
- Bucket List Becomes Swashbuckling Adventure Tour Company
How a small-town Oregonian built a six-figure adventure tour company designing epic trips globally. The Bucket List Lifestyle. Side Hustle School Ep. 735.
- Wedding App Founder Exchanges Vows for Coding Book Biz
Self-taught developer sells beginner coding books via Kickstarter. Hand-delivers worldwide. Side Hustle School Ep. 712.
- Magician Brothers Make Money Appear From Playing Cards
Twin brothers turn cardistry into a profitable playing card deck business. Side Hustle School Ep. 697.
- If At First You Don’t Succeed, Make DIY Journals
Personalized DIY journals with tea-themed designs built by two friends who originally planned a wedding platform. Side Hustle School Ep. 585.
- Independent Musician Strikes Chord With Customized Love Ballads
Independent musician earns $325 per custom love ballad. How personalized songs keep her rent paid. Side Hustle School Ep. 559.
- Marriage Inspires Theatre Captioning App & Service
Theatre captioning service for deaf and hard of hearing audiences, inspired by a musician's marriage. Side Hustle School Ep. 543.
- Policy Researcher Offers Private Tours of Nation’s Capital
How a policy researcher earns $1,500/month with DC private tours on YouTube. Side Hustle School Ep. 508.
- Newlywed Creates Floral Services That Can’t Wilt
Affordable wedding planning service for budget-conscious couples. Side Hustle School Ep. 412.
- Atlanta Duo Gets Paid to Help Engaged Couples Elope
Atlanta couple offers affordable elopement planning as alternative to $35,000 traditional weddings. Side Hustle School Ep. 357.
- Musician Turns Drum Lessons Into Six-Figure Podcast
How a drummer built a six-figure podcast teaching percussion. Started with a borrowed drum set at age 15. Side Hustle School Ep. 296.
- “Dessert Goals” Team Creates Sweet Success
NYC event planners launch desserts-only festival series using social media marketing. Side Hustle School Ep. 284.
- Snapchat Filters for Weddings Lead To $1,400 A Month
How a couple earns $1,400/month designing Snapchat geofilters and wedding programs. They tested products before going all-in. Side Hustle School Ep. 278.
- Writing Duo Makes a Vow To Improve Wedding Speeches
Two writers help couples craft personalized wedding vows and speeches. Built through Yelp and word-of-mouth. Side Hustle School Ep. 271.
- Woman Sells Hair Grips to Orthodox Jews & Drag Queens
How a New Jersey woman earns $4,000/month selling hair grips to Orthodox Jews, cancer patients, and drag queens. Side Hustle School Ep. 268.
- Holiday Body Butters Become $1,000/Month Side Hustle
Body butter side hustle earns $1,000/month on Etsy and craft shows. Holiday gifts spark thriving business. Side Hustle School Ep. 213.
- Food and Travel Writer Creates Food Tours in Marrakech, Earns $60k Annually
How a food writer earns $60k annually running progressive meal tours in Marrakech. Side Hustle School Ep. 201.
- Weekly Recap: Face Painting, Hand Grippers, & Wedding Bells
Weekly recap: face painting, hand grippers, and wedding side hustles — plus listener Q&A on passive income. Side Hustle School Ep. 190.
- Lost & Found: How Lost Property Helps a UK Woman Find Her Side Hustle
Lost property service earns UK woman $70,000 after spotting inefficiency at Glastonbury Festival. Side Hustle School Ep. 189.
- Wedding Bells Ring Brighter if the Bride’s Not Broke
Brittany Haas earns $20,000/month renting luxury bridal accessories with a $50 try-on option. Side Hustle School Ep. 184.
- $10,000 Side Hustle Helps Musician Land Full-Time Job
How a classically trained musician earned $10,000 with music demos and landed a full-time university job. Side Hustle School Ep. 180.
- Designer Illustrates Success with Personalized Wedding Products
Graphic designer earns six figures with personalized wedding products on Instagram and Pinterest. Miss Design Berry. Side Hustle School Ep. 178.
- Epic Scavenger Hunt Becomes 6-Figure Income
How an event planner built six-figures with Cashunt, a competitive scavenger hunt across Boston and beyond. Side Hustle School Ep. 128.
- Renegade Museum Tour Guide Earns $2 Million
How Nick Gray built a $2 million museum tour company from free Met tours. Renegade Museum Hack turned boring into engaging. Side Hustle School Ep. 100.
- WEEKLY RECAP: Karaoke, Tutoring, and Reselling
Weekly recap: karaoke, tutoring, reselling side hustles earning up to $5,000/month—plus listener Q&A. Side Hustle School Ep. 92.
- Academic Advisor Creates Profitable Karaoke League
How Jesse Rauch built District Karaoke from a DC bar night into a five-city league. Side Hustle School Ep. 90.
- Tango Adventures in Buenos Aires
Tango dance lessons and South American group experiences created by a life coach. Buenos Aires adventure trips for women. Side Hustle School Ep. 74.
- NYC Jazz Musician Builds $40,000/Year Blog
NYC jazz musician builds $40,000/year blog and e-course teaching other musicians. Earned $10k in the first launch month alone. Side Hustle School Ep. 69.
- Chicago Psychotherapist Becomes Ceremonial Wedding Officiant
Chicago psychotherapist officiates weddings for extra income. Therapy skills meet ceremony leadership. Side Hustle School Ep. 40.
- Fitness Pole Dance Studio Grows to 4 Locations
How a graphic designer built a pole dance fitness studio to six figures across 4 locations. Sarah quit her day job after year 6. Side Hustle School Ep. 36.