Side Hustle School

By Chris Guillebeau / Onward Project

Business Careers

What's Side Hustle School about?

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.

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#2529 - First $1,000: Data...

12.04.2023

In this week’s First $1,000 segment, we hear from a freelance data visualization expert who turned indecipherable data into compelling narratives. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money ...

Side Hustle School episodes:

12.04.2023 #2529 - First $1,000: Data Specialist Whips Up Custom Reports In this week’s First $1,000 segment, we hear from a freelance data visualization expert who turned indecipherable data into compelling narratives. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money ...
12.03.2023 #2528 - Q&A: “My ADHD makes side hustling hard…” A listener with ADHD is struggling to keep a photography side hustle on track. If you identify as neurodivergent, how can you adjust your productivity strategy? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
12.02.2023 #2527 - Q&A: “An online course for teaching ‘Uncommon Skills…’” Ever thought of turning niche hobbies like unicycling or yo-yo tricks into an online course? That’s what today’s listener has in mind. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra ...
12.01.2023 #2526 - Failure Friday: He Bought a ‘Bored Ape’ NFT for $80,000 In this week’s Failure Friday segment, we hear from an eager enthusiast of digital art. He bought a popular “bored ape” NFT for a lot of money—then watched as the value dropped by 80%. Side Hustle School features a new ...
11.30.2023 #2525 - TBT: Electronic Music Producer Offers Lessons & Mentorship In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an electronic music producer who also coaches other musicians. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ...
11.29.2023 #2524 - Q&A: “Is it too late to plan for holiday sales?” An eCommerce store owner is concerned she's a bit late to leverage the traditional fourth-quarter sales spike. Is it a lost cause? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra ...
11.28.2023 #2523 - Q&A: “A service to help small museums with social media…” Today's caller wants to use her love for art and history to help small museums and galleries improve their social media presence and, in turn, boost visitor numbers. How can she structure this passion into a viable side hustle? Side ...
11.27.2023 #2522 - First $1,000: Birth Chart Consults Aim for Stars In this week’s First $1,000 segment, we hear from a digital age astrologer who sells personalized birth charts, charting the stars for her clients. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ...
11.26.2023 #2521 - Q&A: “Are my Kindle highlights hiding a business opportunity?” How can you manage your Kindle highlights—and is there a business opportunity lurking in this common challenge? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. ...
11.25.2023 #2520 - Q&A: “My enthusiasm fizzles out…” A listener finds himself losing interest in side hustling after an initial burst of enthusiasm. What should you do when your early ideas keep fizzling out? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
11.24.2023 #2519 - Failure Friday: Financial Abundance Coach Charges Too Much In this week’s Failure Friday segment, we hear from a woman who sets out to become a financial abundance coach—but prices her online course too high for her initial clients. Side Hustle School features a new episode EVERY DAY, featuring ...
11.23.2023 #2518 - TBT: Blankets from Nepal Continue to Sell In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a U.K. importer of cashmere blankets. Two years after starting her business, it’s going stronger than ever! Side Hustle School features a new episode EVERY DAY, ...
11.22.2023 #2517 - Q&A: “What are average affiliate commission rates?” How much can you get paid to promote other people’s products? A listener wants to know about the average rates for affiliate commissions. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ...
11.21.2023 #2516 - Q&A: “Can you earn a big DoorDash bonus and then quit?” Chasing after sign-up bonuses in the gig economy can seem like a quick way to boost earnings. It’s not a longterm income source, but once in a while it’s worth it. Side Hustle School features a new episode EVERY DAY, ...
11.20.2023 #2515 - First $1,000: Paralegal Assists U.S. Immigrants to Canada In this week’s First $1,000 segment, we hear from a Canadian paralegal who helps American immigrants learn to navigate the bureaucracy of migration. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ...
11.19.2023 #2514 - Q&A: “My membership site has a high churn rate…” A fitness trainer is grappling with a high churn rate in their membership-based business, compounded by burnout. How can they improve retention? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra ...
11.18.2023 #2513 - Q&A: “A personal stylist for remote workers…” A listener wants to help remote workers look good on screen. Can she monetize her passion for “Zoom fashion”? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting ...
11.17.2023 #2512 - Failure Friday: PayPal Freezes $50,000 in Ticket Fees In this week’s Failure Friday segment, we hear from a first-time event host who sells out a big event—only to discover that PayPal refuses to give him the money. Lots of lessons here! Side Hustle School features a new episode ...
11.16.2023 #2511 - TBT: The Midwest Car Parts Mogul In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a car parts reseller in Missouri who’s been growing his side hustle all the way to six-figures. What can we learn from his story? Side Hustle ...
11.15.2023 #2510 - Q&A: “It’s time to sell my website… how do I do it??” Selling a passion project website can be an emotional journey. Today, we navigate the steps of valuating and selling a site while ensuring it remains in capable and caring hands. Side Hustle School features a new episode EVERY DAY, featuring ...
11.14.2023 #2509 - Q&A: “Can you still profit from blockchain video games?” Ever wondered if playing video games could actually make you money? Today, we look into the world of blockchain video games and assess if they can still be a profitable side hustle. Side Hustle School features a new episode EVERY ...
11.13.2023 #2508 - First $1,000: Video Editor Upgrades from Low-Paying Clients In this week’s First $1,000 segment, we hear from a video editor who starts taking cheap gigs on Fiverr before moving up to serving more valuable clients. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
11.12.2023 #2507 - Q&A: “Should I be a Creator or an Influencer … or neither?” Are you a creator, an influencer, or perhaps a bit of both? Today's listener is curious about the difference between these frequently-used terms Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ...
11.11.2023 #2506 - Q&A: “Does Peak Marketplace mean we’ve reached a saturation point?” Have we hit 'Peak Marketplace,' a point where the online world is too crowded for new entrepreneurs? This caller brings up an alternative perspective to a point I made in Gonzo Capitalism. Side Hustle School features a new episode EVERY ...
11.10.2023 #2505 - Failure Friday: “Remote Year” Nomad Experiences Blogger Burnout In this week’s Failure Friday segment, we hear from a digital nomad who sets out to travel for a year—but soon becomes overwhelmed at the idea of building a business on the road. Side Hustle School features a new episode ...
11.09.2023 #2504 - TBT: Las Vegas Concierge Sells Subscriptions & Savings In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Vegas local who helps tourists save on their visits to Sin City. This is a profitable business for her, bringing in up to $5,000/month part-time. ...
11.08.2023 #2503 - Q&A: “I want to help gamers get fit…” Can you merge the worlds of fitness and gaming into a unique side hustle? Our caller today is a certified trainer looking to tailor workout routines for gamers. Let’s see if we can help him level-up. Side Hustle School features ...
11.07.2023 #2502 - Q&A: “What’s the deal with #BookTok?” What's the business model behind viral book trends on social media like #bookstagram and #BookTok? This listener wants to understand how creators are monetizing book-related content. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
11.06.2023 #2501 - First $1,000: The Canadian Wilderness Experience Curator 1In this week’s First $1,000 segment, we hear from an Alberta man who leads hikes and tours to wilderness areas in his province, incorporating indigenous knowledge and local sites. Side Hustle School features a new episode EVERY DAY, featuring detailed ...
11.05.2023 #2500 - Q&A: “YouTube channel of the Unclaimed Baggage Center…” Tired of the conventional resale game, today's listener is exploring the untapped potential of unclaimed baggage. We break down how his unique blend of unboxing, storytelling, and resale could be an ingenious side hustle. Side Hustle School features a new ...
11.04.2023 #2499 - Q&A: “Help! Mailchimp rejected my newsletter…” Struggling with an email service provider that kicked you to the curb? This episode dives into alternatives and strategies for keeping your email marketing game strong, even when your primary tool bails on you. Side Hustle School features a new ...
11.03.2023 #2498 - Failure Friday: The Handmade Hustle Hassle In this week’s Failure Friday segment, we hear from a handmade jewelry maker who cuts some corners after experiencing an influx of sales. Unfortunately, customers noticed and the efficiency effort backfired. Side Hustle School features a new episode EVERY DAY, ...
11.02.2023 #2497 - TBT: Speaking Agent for Authors Builds Out Roster In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a longtime event planner who transitions to the world of helping authors and experts get paid speaking gigs. Side Hustle School features a new episode EVERY ...
11.01.2023 #2496 - Q&A: “How can you make money from prediction markets?” Ever thought of cashing in on your knack for predictions? Today we explore the world of prediction markets like Augur, Kalshi, and PredictIt. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ...
10.31.2023 #2495 - Q&A: “How can I future-proof my travel blog?” SEO isn't a "set it and forget it" game, especially with emerging technologies like AI and voice search on the rise. Tune in to this episode to discover how to evolve your SEO strategy to maintain high Google rankings. Side ...
10.30.2023 #2494 - First $1,000: Tarot and TikTok Become Winning Combo In this week’s First $1,000 segment, we hear from a tarot card reader who was profitable in one month, all thanks to savvy use of TikTok and smart pricing strategies. Side Hustle School features a new episode EVERY DAY, featuring ...
10.29.2023 #2493 - Q&A: “My sponsored posts have low engagement…” Sponsored posts are often part of a blogger's income—but this British blogger has a problem: the sponsored posts she runs typically have much lower engagement than her organic posts. What can be done? Side Hustle School features a new episode ...
10.28.2023 #2492 - Q&A: “Will my online course cannibalize my freelancing biz?” Diversification is key to financial stability, but could it harm your primary income source? In this episode, a listener seeks help balancing freelancing with an online course offering. Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
10.27.2023 #2491 - FF: Gourmet Chef Gets Lost in the Sauce In this week's Failure Friday segment, we meet a Philadelphia chef who rolled out a gourmet food truck, only to find himself a ghost on the city’s vibrant food scene. Discover how he turned the lessons from his culinary calamity ...
10.26.2023 #2490 - TBT: Ghostwriter Shifts from Happily Ever After to Whodunnit In this week’s 'Throwback Thursday / Where are they now?' segment, we catch up with a ghostwriter who once specialized in romance novels and has since broken into the true crime genre. She shares how market saturation in her original ...
10.25.2023 #2489 - Q&A: “Tax advice for new freelancers…” Tax season can be a nerve-wracking time, especially when juggling a side hustle. Tune in to learn the single most important piece of tax advice that could save you from getting into trouble with the IRS. Side Hustle School features ...
10.24.2023 #2488 - Q&A: “My sister stole my side hustle!” When family and business mix, things can get complicated quickly. In this episode, a side hustler is experiencing tension after her sister pursues a very similar business idea. Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
10.23.2023 #2487 - First $1,000: Comedy Podcast Editor Creates Recurring Income In this week’s First $1,000 segment, we hear from a freelance podcast editor who decided to specialize in comedy shows. From pricing strategies to building efficient systems, hear how he turned his knack for comedic timing into a money-making side ...
10.22.2023 #2486 - Q&A: “I haven’t sent an invoice in two years…” In today’s episode, a tutor grapples with the absence of a formal invoicing system in his two-year-old math tutoring side hustle. Let’s fix that! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ...
10.21.2023 #2485 - Q&A: “I feel defeated by the Instagram algorithm…” Struggling with Instagram's fickle algorithm and the emotional toll of low engagement? Tune in for actionable hacks to beat the system and keep your sanity intact. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
10.20.2023 #2484 - Failure Friday: The Autumn Sweater Stockpile Saga In this week's Failure Friday segment, we hear from a retailer who gambled half her startup capital on a massive inventory of holiday sweaters, only to watch the season—and her profits—melt away. Learn how she navigated the fallout to come ...
10.19.2023 #2483 - TBT: Sustainability Consultant Finds Side Hustle at Day Job In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a sustainability consultant who discovered her first client from an unexpected source: her employer! Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
10.18.2023 #2482 - Q&A: “Is there a market for cool driftwood art?” An artist makes local driftwood into unique pieces of art. How can she cash in this treasure? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. ...
10.17.2023 #2481 - Q&A: “I’m seeing slow growth after three months of side hustling…” A Boston-area listener started a consulting service, but it’s not taking off in the way she hoped. How should she proceed? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money ...
10.16.2023 #2480 - First $1,000: “Virtual Study Buddy” Offers Motivational Tutoring In this week’s First $1,000 segment, we hear from an educational psychologist who combined traditional tutoring with motivational coaching. Learn how targeted pricing, grassroots marketing, and client retention helped her offer a unique service Side Hustle School features a new ...

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