The Side Hustle Show
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Latest episodes
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767: Listeners Share Their Scariest Entrepreneurial Moments
October 29, 2026 · 44 minWhat’s the scariest moment you’ve faced as an entrepreneur? For Halloween, I asked Side Hustle Show listeners to share theirs. You’ll hear about a 1.1 million-follower Instagram account deleted overnight, a Google update that wiped out…
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766: We Found Reddit’s Weirdest Side Hustles
October 22, 2026 · 55 minCan you really make money in tickling tomato flowers or selling your own boogers? Today's episode digs into a pile of genuinely bizarre side hustles pulled from Reddit threads, and most of them actually work. Alan Donegan from The Rebel…
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How to Start a Commercial Cleaning Business on the Side: $100k in 9 Months (Greatest Hits)
October 19, 2026 · 47 minThis week’s guest booked $100k worth of commercial cleaning business in her first 9 months. Haley Gallagher and her husband are serial side hustlers and were specifically looking for a side hustle they could do after hours. Seeing an…
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765: The $50k/mo One-Person Agency
October 15, 2026 · 54 minCan one person run an AI consultancy without hiring a team of developers? Simon Bergeron runs Lemonbrand.io, a one-person business that’s part digital agency, part consultancy, with some micro SaaS on top. He manages a team of about 500…
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764: 17 Surprising Businesses That Can Make Millions
October 8, 2026 · 50 minWhat do hermit crab food, glitter bombs, and dog sunglasses have in common? They're all real businesses making real money by solving weird, specific problems nobody else wanted to touch. Steve Chou, from My Wife Quit Her Job, is back for…
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763: He Makes $3,000 a Year Every Time He Gives a Restaurant a Free Chalkboard (And He’s Done it 200+ Times)
October 5, 2026 · 46 minWhat if you could earn $3,000 a year from a whiteboard you give away for free? John Schierman of MegansDailyDish.com places free chalkboards and whiteboards in restaurants and other busy venues. The venue uses the board for daily…
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762: Buy Buttons, 10 Years Later
October 1, 2026 · 59 minWhat if the hardest part of your business isn't building the thing, but finding someone to buy it? Ten years ago, I wrote a book called Buy Buttons. The premise: instead of building a store or website and hoping somebody finds it, go set…
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$1000 a Week Tutoring on the Side (Greatest Hits)
September 24, 2026 · 47 minThe ACT is a college entrance exam used by many colleges to rank students applying to their schools. The subject matter covers English grammar, reading comprehension, math, and science. Millions of students take the test each year and the…
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761: Shopping for Cash Flow: Buying an Online Business in 2026
September 21, 2026 · 46 minWhat if you could skip the hardest part of starting a business, the zero-to-one grind, and just buy your way into cash flow instead? Joe Burrell runs Just Website Brokerage, where he's helped broker over 300 sales totaling more than $7…
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760: The $100k/mo Single-Function Site, the $4k Pet Party Planner, the $30k Cheese Fortune Teller, and more
September 17, 2026 · 56 minToday, we're digging into a stack of side hustle examples and brainstorming ways you could put your own spin on it. To help me out, I invited Deacon Hayes back on the show. Deacon is the founder of WellKeptWallet.com and the author of You…
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759: Zero to $20k/mo with the Amazon Influencer Program
September 10, 2026 · 1 hr 3 minWhat if the easiest money you ever made online came from filming your own bathroom, your neighbor's Legos, or a handwashing station at a farmer's market? Nate Jackson from Hustle Buddies is back on the show to talk about the Amazon…
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758: From Zero to $120k/mo in 18 Months
September 7, 2026 · 53 minCan you build a six-figure e-commerce business selling products you don't even use yourself? Let's find out. 18 months ago, today's guest was working a day job in digital marketing, feeling like he was always building somebody else's…

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