Chris Guillebeau
Side Hustle School
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. Hosted on Acast. See acast.com/privacy for more information.
Author
Chris Guillebeau
Category
Podcast website
Latest episode
Jul 11, 2026
Where to listen?
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Episodes
Ep. 2982 - Q&A: “How do I get media coverage for my small business?” 01.03.2025 5:38
In this episode, we help a sustainable home goods brand owner break into the media spotlight. Learn simple, budget-friendly strategies for getting press coverage without hiring a PR agency. 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&am...
Ep. 2981 - Q&A: “How can I edit course videos efficiently on a budget?” 28.02.2025 5:10
In this episode, we help an online course creator level up her video editing skills on a budget. Learn beginner-friendly tools and smart tips for producing polished videos without breaking the bank. 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 list...
Ep. 2980 - TBT: Production Assistant Specializes in Props Sourcing 27.02.2025 5:36
In this week's Throwback Thursday segment, we hear from a Vancouver production assistant who built a side hustle around sourcing hard-to-find props. Discover how filling an unusual niche brought steady work and new credibility in a competitive industry. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Th...
2979 - Former Construction Inspector Helps Students Pass Exams 26.02.2025 5:51
A teacher-turned-construction inspector aces his exams and creates a series of courses to help others entering the field. 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: SideHustleSchool.com Email:...
Ep. 2978 - Q&A: “How can I grow my streaming audience?” 25.02.2025 4:44
In this episode, we explore how a college gamer can grow their audience and increase their chances of monetization. Streaming success isn't just about going live! 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....
Ep. 2977 - First $1,000: Social Media Captions Turn Into Passive Income 24.02.2025 5:45
In this week's First $1,000 segment, we explore how an Arizona writer turned her knack for social media into a business, creating quick, effective posts for busy freelancers. 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 day...
Ep. 2976 - Weekend Workshop: Crafting a Compelling Offer 23.02.2025 6:46
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: crafting a compelling offer. 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, t...
Ep. 2975 - Q&A: “How do I handle blog questions without feeling overwhelmed?” 22.02.2025 4:49
In this episode, we help a health blogger handle an influx of reader questions without feeling overwhelmed. Learn how to stay engaged with your audience while managing your time effectively. 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...
Ep. 2974 - Q&A: “Where should I host my online course?” 21.02.2025 5:47
In this episode, we help a history professor decide how to launch an online course. Should he use a big platform like Udemy or host it independently—and how can he attract an audience for a niche topic? 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 lesson...
Ep. 2973 - TBT: Turning Late-Night Edits into a Niche Agency 20.02.2025 7:07
In this week's Throwback Thursday segment, discover how one freelancer turned scattered editing gigs into a specialized agency serving fitness creators, creating sustainable 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, the show includes free guided lessons and listener Q&am...
Ep. 2972 - STORY: 13-Year-Old Australian Creates Schoolyard Lollipop Fortune 19.02.2025 7:07
This enterprising Aussie teen sells 50+ lollipops a day, earning a 100% profit margin and drawing a crowd of happy customers that follow the sound of her jangling pockets. 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 e...
Ep. 2971 - Q&A: “Should I keep offering a service that’s profitable but draining?” 18.02.2025 5:10
In this episode, we help a graphic designer evaluate whether it's time to let go or find a way to make it work better. How do you handle a service that's profitable but takes a toll on your energy? 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 liste...
Ep. 2970 - First $1,000: Mystery Gift Bundles for the Indecisive Shopper 17.02.2025 5:24
In this week's First $1,000 segment, we hear from a side hustler who helps shoppers choose the perfect gift. Find out how her mystery bundles became a hit with customers who love the surprise factor. 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...
Ep. 2969 - Weekend Workshop: Finding Your Ideal Customer 16.02.2025 7:29
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: understanding your ideal customer. 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...
Ep. 2968 - Q&A: “How do I handle customer refunds without ruining my cash flow?” 15.02.2025 5:27
In today's episode, we help an online shop owner navigate the tricky balance of customer satisfaction and financial stability. Refund requests don't have to derail your business—discover how smart strategies can make all the difference. 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...
Ep. 2967 - Q&A: “Is Valentine’s Day worth targeting if my product isn’t romantic?” 14.02.2025 4:39
In this episode, we explore how to run holiday promotions—even if your product doesn't naturally fit the season. Learn creative ways to tie your business into major holidays without feeling forced. 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...
Ep. 2966 - TBT: How SEO Support Became a Reliable Monthly Payday 13.02.2025 5:57
In this week's Throwback Thursday segment, discover how a freelance SEO auditor transformed one-time reports into a thriving monthly subscription, offering clients fresh keywords, competitive insights, and ongoing support. 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...
Ep. 2965 - STORY: Coffee Lover Bets Beans On Workplace Coffee Subscriptions 12.02.2025 6:39
A corporate HR professional turns his love for coffee into a fully brewed side hustle. 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the...
Ep. 2964 - Q&A: “How can I build trust in a tax service for digital nomads?” 11.02.2025 4:08
In today's episode, we help an accountant build trust with digital nomads and scale her international tax service. Learn how to establish credibility, stay on top of regulations, and grow with confidence. 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 an...
Ep. 2963 - First $1,000: London Underground Photo Safaris 10.02.2025 5:46
In this week's First $1,000 segment, we hear from a London photographer who created urban photo safaris for tourists. Learn how they combined hidden gems and photography lessons to get booked over and over. 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...
Ep. 2962 - Weekend Workshop: Become a Side Hustle Detective 09.02.2025 6:36
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: learning from others' success. 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,...
Ep. 2961 - Q&A: “What’s the best way to pre-sell a product I haven’t made yet?” 08.02.2025 5:14
Can you sell a product that doesn't fully exist yet? In this episode, we help an engineer navigate the world of pre-sales, with tips on how to test demand while building trust with potential customers. 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 l...
Ep. 2960 - Q&A: “How to price your services without undervaluing your expertise?” 07.02.2025 5:23
In today's episode, we help a fitness trainer navigate the tricky balance of pricing her postpartum workout plans. Learn how to offer options for different budgets and build a sustainable business—while staying true to your mission. 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...
Ep. 2959 - TBT: Personalized Travel Itineraries for Digital Nomads 06.02.2025 6:21
In this week's Throwback Thursday segment, discover how a travel lover in Lisbon began crafting personalized itineraries for remote workers, helping them find coworking gems and local culture—while earning a solid 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, the show includes...
Ep. 2958 - STORY: Florida Man Leads Scooter Tours After Watching Macklemore Video 05.02.2025 6:56
Had a broken keyboard, bought a broken keyboard: this corporate refugee relocates to Florida and kicks off a new hustle leading adult scooter tours. 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: S...
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