A daily show for everyone who works a regular job and wants to start an income-earning project on the side. In each episode, listeners will hear a different story of someone who's started a side hustle—along with what went well, how that person overcame challenges, and what happened as a result. The show is written and hosted by Chris Guillebeau, the New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, and other books. Sales and Distribution by Lemonada Media http ...
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Chris Guillebeau / Onward Project Podcasts
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Ep. 3220 - Q&A: “When is business coaching worth the cost?”
5:35
5:35
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5:35Coaching can fast-track growth—or drain a lot of money from your bank account. In this short episode, you’ll learn a simple metric to decide whether a pricey mentor is a smart bet or a motivational luxury. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. …
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Ep. 3219 - Q&A: “Can I sell carbon-offset checks to small brands?”
5:54
5:54
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5:54Green-washing headlines have everyone nervous, and for good reason. Today we design a “quick-check” carbon-audit service small brands will pay for—and keep the workload under two hours per client. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year…
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Ep. 3218 - TBT: I Built a Supplement Guide People Actually Trust
5:50
5:50
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5:50In this week’s Throwback Thursday segment, learn how a side hustler built a trustworthy supplement guide from one TikTok video, turning it into a $40,000 affiliate business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes fre…
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Ep. 3217 - STORY: Aussie Stretches Out with Online Store for Tall Women
7:02
7:02
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7:02Tall women everywhere rejoice as an eCommerce side hustle brings new meaning to ‘top shelf.’ Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleS…
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Ep. 3216 - Q&A: “How do I avoid a garage full of unsold kits?”
5:05
5:05
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5:05Should you spend months growing followers or risk cash on inventory right away? Today we outline a “test-then-preorder” strategy that proves demand in weeks, pays for production up front, and builds your email list as you go. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without …
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Ep. 3215 - First $1,000: Board-Game Date Nights in a Café Basement
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5:54In this week’s First $1,000 segment, hear how a board-game collector transformed an unused café basement into a candle-lit playground for couples. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listen…
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Ep. 3214 - Weekend Workshop: From Spreadsheets to Six Figures
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7:04
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7:04This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: the original spreadsheet king. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra …
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Ep. 3213 - Q&A: “Can I monetize a college scholarship database?”
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5:01Obscure college scholarships are gold, at least if parents trust your data. In this episode we design a subscription, ROI guarantee, and tech stack that can turn a spreadsheet into monthly income. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year…
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Ep. 3212 - Q&A: “Will people pay for AI-optimized resumés?”
5:09
5:09
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5:09Cheap resumé bots and pricey human writers leave a gap. We’ll show how an AI-plus-expert service can fill it, both profitably and credibly. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A …
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Ep. 3211 - TBT: Built in a Weekend, Used by Thousands
5:11
5:11
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5:11In this week’s Throwback Thursday segment, hear how a side project built over a single weekend turned into a surprisingly steady income stream, all thanks to a clunky but useful Chrome extension with 5,000 loyal users. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quittin…
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Ep. 3210 - STORY: Canadian Bidets Modernize Bathroom Life
7:42
7:42
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7:42In several parts of the world, bidets are used in lieu of toilet paper—but why not in Canada? One man sets out to change that, flushing away discouragement and banking profits. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes …
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Ep. 3209 - Q&A: “How do I use exit pop-ups?”
4:44
4:44
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4:44A well-timed nudge can rescue sales, but only if it feels like service, not a race to the bottom. Let’s design a polite “please stay” offer that boosts revenue without creating coupon addicts. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, th…
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Ep. 3208 - First $1,000: Vintage Sewing Machine Rehab Workshops
5:29
5:29
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5:29In this week’s First $1,000 segment, meet the maker who buys twenty-dollar thrift-store sewing machines, teaches students to revive them, and lets each participant leave with a fully functioning vintage Singer. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their …
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Ep. 3207 - Weekend Workshop: The Global Photography Pivot
6:45
6:45
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6:45This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: a nomadic photography business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra…
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Ep. 3206 - Q&A: “How do I fight piracy without hurting buyers?”
4:51
4:51
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4:51You can’t stop every pirate, but you can slow them down—and keep real customers smiling. Today we cover low-cost deterrents, “soft DRM,” and community perks that make stealing less attractive. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, th…
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Ep. 3205 - Q&A: “How do I license calming coloring pages to wellness apps?”
4:48
4:48
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4:48Trade $2 one-time sales for four-figure B2B deals. We build the pitch, pricing, and contract essentials for licensing art to wellness platforms. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener…
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Ep. 3204 - TBT: The Secret Author Behind Your Favorite Romance Novel
5:20
5:20
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5:20In this week’s Throwback Thursday segment, hear how one fanfiction writer went pro—now earning five figures per project ghostwriting for bestselling romance authors who don’t want their names published. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Thi…
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Ep. 3203 - STORY: Underwear Side Hustle Turns Into $500,000/Month Business
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7:00By Chris Guillebeau / Onward Project
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Ep. 3202 - Q&A: “Can a ‘tech deals’ newsletter really make money?”
3:49
3:49
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3:49By Chris Guillebeau / Onward Project
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Ep. 3201 - First $1,000: Weekend ASL Crash Courses for Hospitality Staff
4:59
4:59
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4:59In this week’s First $1,000 segment, hear how a certified interpreter turned empty hotel conference rooms into a training ground for quick, practical American Sign Language (ASL). Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includ…
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Ep. 3200 - Weekend Workshop: From Utah Piano Teacher to Digital Nomad
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5:57
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5:57This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: a $360,000/year online music school. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn …
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Ep. 3199 - Q&A: “How do I handle a non-compete that hurts my side hustle?”
5:09
5:09
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5:09A promotion with strings attached can stall a thriving side hustle. Today we’ll walk through reading the fine print, negotiating carve-outs, and keeping both your boss and your business on the road. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This ye…
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Ep. 3198 - Q&A: “I went viral, but now I can’t meet demand!”
5:23
5:23
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5:23A viral spike is great—until it breaks your capacity. Today we map a four-step triage plan to pause the chaos, satisfy customers, and turn overwhelm into long-term buzz. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free gu…
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Ep. 3197 - TBT: Turning Property Management Experience Into Digital Products
5:32
5:32
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5:32In this week’s Throwback Thursday segment, learn how one former apartment manager turned their real estate experience into a template shop for landlords, helping them boost revenue without buying new properties. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their…
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Ep. 3196 - STORY: Google Employee Makes $100,000 Using Fiverr
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7:32
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7:32In just one year, this Google product manager earned an extra $100,000 by providing marketing services on Fiverr.com. Learn his tips to hack the platform for yourself! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guid…
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