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*An audiobook-y podcast about how work, dating and making rent sucks.* Making rent in NYC is hard. Really hard. And no one knows that better than 20-something failed journalist, Ally Mehta. After losing her job and apartment in one day, she's forced to resort to drastic measures to find a new living situation: Tinder. With just 30 days left on her lease, Ally decides that instead of looking for a roommate, she'll look for a live-in boyfriend. After all, nothing is cheaper than splitting rent ...
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Side Hustle School

Chris Guillebeau / Onward Project

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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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Being positive is up to you. When you understand how your mind works, you really can create the life you desire. The Be Positive Podcast is your weekly reminder that no matter what you're going through, there’s always a reason to stay hopeful, stay focused, and stay positive. Through real talk, uplifting messages, and personal stories from listeners around the world, I'll help you tap into your inner strength, shift your mindset, and see life from a brighter perspective. Whether it’s finding ...
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Today’s listener wants to turn store returns into cash. We’ll cover how to evaluate a pallet, estimate true margins, and avoid getting stuck with dead inventory. 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 les…
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AI is everywhere these days. It is writing emails, answering questions, making dinner reservations, and probably judging our spelling mistakes behind the scenes. With so much noise and nonstop tech talk, it is fair to ask the big question. Are you tired of AI yet? In this episode of the Be Positive Podcast I slow things down and get real about our …
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In this week’s First $1,000 segment, campus recruiters needed polished LinkedIn photos—but photographers were booked solid. One creative grad built a plug-and-play headshot booth, rented it four times in a month, and snapped up his first grand without clicking the shutter himself. Side Hustle School features a new episode EVERY DAY, featuring detai…
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This 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 small-scale, large-reach transcription business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of pe…
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Today’s caller makes more money on weekends than at the day job—but their revenue graph looks like a heart monitor. Can they rely enough on their extra income to go all-in? 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…
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If clients praise your speed but you’re still billing like a beginner, it’s time to level up. Today we pinpoint the three value levers that justify higher VA rates—and a script that keeps loyal clients on board. 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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In this week’s Throwback Thursday segment, find out how one patient side hustler stockpiled retired LEGO sets, held them like collectibles, and eventually parlayed the profits into a full-on store. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This yea…
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After relocating to Quebec, this continental creative brings seasonal flavor to an artisanal food retailing biz. 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. Sho…
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Are you just tired—or do you need a bigger break? In this episode, we’ll help a listener take a stress-test to know if they need rest, a redesign, or a full business pivot. 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…
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In this week’s First $1,000 segment, a designer helps food trucks and pop-up restaurants get rid of chalk dust and update to the digital age. 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&…
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This 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: an online snow-skiing school. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra m…
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Is your life zooming past you like it’s late for work and forgot to put on pants? In this episode of the Be Positive Podcast, I'm hitting the brakes and talking about how to slow that runaway train we call life. Because you deserve more than just “getting through the day.” You deserve to experience it. We’re diving into the simple mindset shifts, t…
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Today’s caller runs a tiny subscription app and has two grand to spend. Should that money patch cancelations or chase new sign-ups? We’ll do the napkin math and land on a clear next step. 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 sho…
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Posting everywhere spreads you thin; posting in the right place compounds momentum. Today we break down a three-question filter that shows exactly where this side hustler’s wallets should live first. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This y…
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In this week’s Throwback Thursday segment, hear how one copy-savvy side hustler turned a collection of recruiter emails into a paid “swipe file,” and then built a monthly subscription around it. 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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The buzzworthy journey of Minnesotan bees and their keepers. These hardy bees don’t mess around—last year they produced $150,000 in sweet 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 free guided lessons and listen…
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Great contracting work often reveals the next problem to solve. Here’s a simple script that turns an “upsell” into an obvious win for the client—and leaves everyone feeling good about the extra invoice. 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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A bedtime-reading addict bend a paperclip into a page holder, refines it into a soft-touch clip, and flips his ledger from red ink to a four-figure win. 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 …
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This 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: how a single PDF guide earned $120,000 in its first year. Side Hustle School features a new episode EVERY DAY, featuring detailed case studie…
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Remote-worker visas are booming—and bewildering. Today we price a “visa concierge,” unpack simple liability safeguards, and gauge whether the market can pay more than pocket change. 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 incl…
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AI tools can double your output, but not everyone’s comfortable with it. Today we map a three-part policy for disclosing AI use that keeps trust high, quality higher, and clients on board. 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 sh…
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In this week’s Throwback Thursday segment, meet a side hustler who built a simple browser-based spreadsheet tool. It earns enough to cover his rent each month! 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 lesso…
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After creating course materials for a forgotten group of educators, this agricultural teacher now earns a significant income from a growing 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 free guided lessons and lis…
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Can busy side hustlers trade skills instead of dollars? Today we outline a lean time-bank model—simple rules, low overhead, and real incentives to keep everyone honest. 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 gui…
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Tired of cables dangling each time your standing desk rises? A quick TikTok clip of magnetic rails snapping cords into place sparked a rush of orders for this savvy side hustler. 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 include…
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Are You Winning or Accepting Losing? In this episode, we dive deep into the mindset that shapes how we show up in life. Are you truly pushing forward toward your goals, or have you quietly settled for less than you deserve? Sometimes we call it “peace,” but it’s really acceptance of defeat. Let’s get honest about where we’ve stopped fighting for ou…
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This 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: an early language hacker starts “Fluent in 3 Months.” Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of…
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Cash can launch the product; labor will keep it alive. Today we map out founder-friendly splits, vesting schedules, and a simple “dynamic equity” formula that grows with effort. 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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One sale beats a hundred compliments. Let’s walk through a low-risk, weekend-ready plan that puts money in this side hustler’s hands within two weeks. 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 li…
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In this week’s Throwback Thursday segment, learn how one fitness fan turned flipping gym equipment into a small media business. He now sells setup guides and curates weekly home gym deals for thousands of subscribers. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting…
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I hear ya. After a brief thought of calling it quits with the podcast, you made it clear that I need to continue to share my positivity. If you're reading this, I want you to know you inspire me! Thank You. Enjoy the podcast. The Be Positive Podcast is your weekly reminder every Monday, that no matter what you're going through, there’s always a rea…
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Rise and shine! A petroleum engineer finds the perfect item to resell on Amazon. He goes on to sell $300,000 worth of the humble coffee grinder. 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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Free traffic feels safe, but paid ads might unlock a faster lane—IF the math checks out. Let’s design a two-week, $200 ad test with clear “go / no-go” numbers so this side hustler can see truth, not guesswork. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their j…
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Welcome to a new episode where we explore the cost of spiritual awakening, particularly in our relationships. Can personal growth and increased understanding come at the expense of our connections with a friend? Let's discuss the importance of self help and empathy as we navigate these complex dynamics. The Be Positive Podcast is your weekly remind…
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Shopify merchants kept begging forums for the same quick theme fixes. One developer bundled all his proven snippets behind a $15 monthly paywall—and 170 store owners are happily copying, pasting, and paying. 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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This 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: if he hadn’t been pushed, he wouldn’t have made the leap. Side Hustle School features a new episode EVERY DAY, featuring detailed case studie…
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TikTok, Snap, and Instagram fame is fun, but e-mail tends to pay the bills. Today we lay out the follower-to-inbox conversion math, including the moment a list becomes non-negotiable. 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 in…
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Old barns can be gold mines—or legal landmines. Today we cover permits, insurance, and realistic margins for turning reclaimed boards into profit. 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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In this week’s Throwback Thursday segment, learn how a creative project for a friend in recovery became a business, eventually leading to a partnership with a Washington, DC nonprofit. 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 i…
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A chef sets out to reinvent the humble apron, growing it to a multi-million-dollar company while still working in restaurants at night. 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 seve…
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Today’s caller wonders whether to polish the package or finish the product. We’ll set a two-checkpoint rule that keeps creativity flowing, without turning branding into busywork. 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 include…
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In this week’s First $1,000 segment, meet the HubSpot whiz who charges Realtors $500 for a three-hour CRM detox—merging duplicates, tagging leads, and automating follow-ups before lunch. 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…
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This 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 $100 Alaska coupon book that sells over and over. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of…
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Coaching 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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You got everything you thought you wanted the job, the love, the peace, the success yet somewhere in the quiet corners of your mind, negativity still lingers. Why? In this episode, we peel back the glossy surface of “having it all” to explore the deeper truth about happiness, fulfillment, and the mind’s sneaky habit of moving the finish line. This …
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Green-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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In 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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Tall 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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Should 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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In 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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