The Side Hustle Show
Nick Loper of Side Hustle Nation | YAP Media
The entrepreneurship podcast you can actually apply! The award-winning small business show covers creative ways to make money online and offline, including online business, side gigs, freelancing, marketing, e-commerce, AI tools, investing, and much more. Join 150,000+ listeners and get legit business ideas and passive income strategies straight to your earbuds. No BS, just actionable tips on how to start and grow your side hustle. Hosted by Nick Loper of Side Hustle Nation since 2013.
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For ad inquiries, please reach out to: [email protected]
Episodes
Mentioned books
Oct 29, 2026 • 44min
767: Listeners Share Their Scariest Entrepreneurial Moments
Entrepreneurs share their most terrifying business moments: a million-follower account vanishing, Google updates gutting income, inventory disasters, 10,000 ruined DVDs, and a Bitcoin ransom scam. Other stories explore quitting stable jobs, leaving an eight-figure company, and laying off a beloved team. A gripping collection of entrepreneurial scares, risky leaps, and hard-earned recoveries.
21 snips
Oct 22, 2026 • 55min
766: We Found Reddit’s Weirdest Side Hustles
Alan Donegan, entrepreneur and co-founder of The Rebel School, explores Reddit’s strangest money-making ideas. Discover rare roly-poly breeding, soda-tab sales for cosplay, paid line waiting, tomato pollination, cat-themed tours, wedding crying, and more. The conversation uncovers how weird ventures solve annoying problems, serve passionate niches, repurpose free materials, and grow through partnerships and word of mouth.
17 snips
Oct 19, 2026 • 47min
How to Start a Commercial Cleaning Business on the Side: $100k in 9 Months (Greatest Hits)
Haley Gallagher, entrepreneur and co-owner of Moonlight Commercial Cleaning, turned a bar cleaning opportunity into $100,000 in booked business in nine months. She shares how early customers came through networking, Facebook, and Angi, plus the realities of pricing, hiring night cleaners, managing payroll, and scaling while raising a family. Expect lessons from rapid growth, staffing challenges, and building systems for recurring commercial work.
45 snips
Oct 15, 2026 • 54min
765: The $50k/mo One-Person Agency
Simon Bergeron, founder of Lemonbrand.io, runs a one-person AI consultancy powered by hundreds of agents. He discusses serving small and midsize teams, landing early clients, and his “measure first, then automate” approach. Topics include inbox audits, AI Sherpa retainers, client-owned infrastructure, agent safety, and evolving from consulting into micro-SaaS.
12 snips
Oct 8, 2026 • 50min
764: 17 Surprising Businesses That Can Make Millions
Steve Chou, e-commerce entrepreneur, educator, and creator of My Wife Quit Her Job, returns with a wild tour of businesses built around overlooked opportunities. Discover niche pet products, glitter bombs, dung paper, cardboard furniture, 3D-printed novelties, lost luggage, and more. They also explore viral marketing, emotional purchases, AI automation, and why even grief, fear, and humor can fuel profitable products.
10 snips
Oct 5, 2026 • 46min
763: He Makes $3,000 a Year Every Time He Gives a Restaurant a Free Chalkboard (And He’s Done it 200+ Times)
John Schierman, entrepreneur behind Megan’s Daily Dish, has placed 200+ sponsored chalkboards in restaurants and busy venues. He discusses securing locations, selling recurring ad spots, choosing ideal local advertisers, and using referrals to fill inventory. He also explores scaling across cities, remote tools, ad design, maintenance, and expanding board relationships into broader marketing services.
8 snips
Oct 1, 2026 • 59min
762: Buy Buttons, 10 Years Later
A decade after Buy Buttons, marketplace opportunities have evolved. Explore Etsy, Amazon, Fiverr, eBay, Whatnot, Outschool, and Teachers Pay Teachers, plus platform-driven ideas like laundry services and Facebook Marketplace reselling. The discussion also ventures offline, showcasing coffee bikes, aura photography, dress rentals, and vending machines where location can make or break sales.
Sep 24, 2026 • 47min
$1000 a Week Tutoring on the Side (Greatest Hits)
Matt Fuentes, educator and founder of Take Aim Tutoring, shares how he built a thriving SAT and ACT prep business alongside teaching. He discusses landing his first clients, turning referrals and counselor partnerships into a steady lead source, and moving sessions online with Zoom. Plus, free workshops, premium pricing, online courses, and building a vetted tutor network.
23 snips
Sep 21, 2026 • 46min
761: Shopping for Cash Flow: Buying an Online Business in 2026
Joe Burrell, founder of Just Website Brokerage, has brokered 300+ online business sales since 2012. He and Nick Loper tour live listings, from content sites and e-commerce stores to SaaS and faceless YouTube channels. They explore profit multiples, due diligence, seller financing, AI-era risks, traffic diversification, and the post-purchase plans that keep acquisitions from falling apart.
23 snips
Sep 17, 2026 • 56min
760: The $100k/mo Single-Function Site, the $4k Pet Party Planner, the $30k Cheese Fortune Teller, and more
Deacon Hayes, founder of Well Kept Wallet, personal-finance author, and serial entrepreneur, explores unconventional money-makers. They spotlight a simple website earning six figures monthly, pet parties, line-dancing lessons, cheese-based entertainment, and paid robot-training tasks. Hayes also shares his Facebook content system, AI-powered ad tracking, and his surprising leap into making a clean rap album.
