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.
Vizitează neapărat site-ul podcastului și susține-i creatorul: sidehustleschool.com
Autor
Chris Guillebeau
Categorie
Site-ul podcastului
Cel mai nou episod
27 oct. 2026
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Episoade
#2915 - Q&A: “Best tools for managing a shared business inbox?” 24.12.2024 4:54
In today's episode, we help a listener find the best way to co-manage a business email account with their team, including HelpScout, Hubspot, and more. 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...
#2914 - First $1,000: Data Analyst Codes Fantasy Sports Teams 23.12.2024 6:14
In this story, we follow a data analyst who turns his knack for numbers and love of sports into a profitable business. We explore how he developed fantasy sports prediction algorithms that helped him reach his first $1,000 in earnings. 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...
#2913 - Q&A: “How do I understand ROI when buying a local business?” 22.12.2024 4:57
In today's episode, we help a listener understand how to calculate ROI when considering buying a local business. We'll cover how to estimate the payoff period, factors that impact profitability, and tools to make the analysis easier. 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...
#2912 - Q&A: “I’ve been paying for subscriptions I don’t use!” 21.12.2024 5:15
In today's episode, we help a listener figure out what to do after paying for multiple subscriptions they haven't used: a common and unfortunate problem. 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 not...
#2911 - Failure Friday: When My Side Hustle Took Over My Life 20.12.2024 7:16
In this week's “Failure Friday” segment, we hear from a tech professional who started offering design and development services as a side hustle. As the business grew, balancing it with a full-time job and personal life becomes overwhelming, leading to stress and performance issues at work. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people wh...
#2910 - TBT: Graphic Artist Taps Into Planner Craze 19.12.2024 6:19
In this week's “Throwback Thursday” segment, we hear from a side hustler whose passion for organization and design morphed into a steady income stream while maintaining her day job. 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...
#2909 - Q&A: “How can I increase the average price per order for my online store?” 18.12.2024 4:21
In today's episode, we help a listener with strategies to boost the average order value of her online store. We'll cover upselling, cross-selling, and other techniques to increase sales in a way that feels natural and customer-friendly. 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...
#2908 - Q&A: “Should I hire micro-influencers to promote my brand?” 17.12.2024 5:54
In today's episode, we help a listener decide whether to use micro-influencers to promote their e-commerce brand. Should they hire through an agency or go the DIY route to save money? 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 se...
#2907 - First $1,000: Managing Airbnb Properties in Amsterdam 16.12.2024 6:19
In this week's “First $1K” segment, we hear from a Dutch side hustler who turned her organizational skills into a profitable business by managing Airbnb properties for homeowners. 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&...
#2906 - Q&A: “I need a sales script for cold emailing potential clients!” 15.12.2024 5:18
In today's episode, we help a listener refine their cold email strategy to get more client responses. Learn how to craft personalized, value-driven messages that convert, without sounding like a template. 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...
#2905 - Q&A: ““What’s the best ticketing strategy for my event?” 14.12.2024 4:33
Today's episode tackles a question about the best way to sell tickets for an event. Should you keep sales open on a rolling basis or create urgency with a waitlist and limited sale dates? 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&...
#2904 - Failure Friday: Mobile Massage Service Gets Shut Down 13.12.2024 6:09
In this week's “Failure Friday” segment, we hear from the owner of a mobile massage service who set up shop in front of a busy mall, only to get shut down by mall management. Oops! 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...
#2903 - TBT: Santa's Secretary Sees Seasonal Surge 12.12.2024 4:50
In this week's “Throwback Thursday” segment, we hear from the “Letters from Santa" operator whose side hustle has experienced significant growth in the past two years. She now earns more than $25,000 each holiday period. 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...
#2902 - Q&A: “How can I start a digital side hustle with no experience?” 11.12.2024 4:56
In today’s episode, we help a listener who’s brand new to the digital space figure out where to start with their side hustle. We’ll cover the first steps for getting online, building an audience, and setting yourself up for long-term 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, th...
#2901 - Q&A: “Should you start a new hustle or scale what you already have?” 10.12.2024 3:53
Today’s episode tackles a question from a listener wondering whether to start a new side hustle or focus on scaling their current one. We explore both approaches and provide tips to help you choose the best path forward. 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 g...
#2900 - First $1,000: Handyman Cashes In On Home Theater Boom 09.12.2024 6:51
In this week’s First $1,000 segment, we hear from a DIY enthusiast who turned his knack for TV wall mounting into a profitable side hustle—without actually mounting any TVs himself. 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...
#2899 - Q&A: “Can you profit on OnlyFans with non-adult content?” 08.12.2024 5:47
In today’s episode, we explore the opportunities for non-adult content on OnlyFans. From fitness coaching to creative arts, discover how you can build a loyal audience—while remaining fully clothed! 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...
#2898 - Q&A: “What are the hardest side hustles to start and operate?” 07.12.2024 5:54
In today’s episode, we discuss the hardest side hustles to start and manage. From fashion businesses dealing with inventory headaches to restaurants with high overhead costs, learn which side hustles come with the most challenges. 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 inclu...
#2897 - Failure Friday: "Good Political News" Channel Runs Out of Stories 06.12.2024 7:22
In this week’s “Failure Friday” segment, we hear from a content creator who launches a YouTube and TikTok channel focused on sharing uplifting political stories, inspired by popular "good news" channels. Unfortunately, finding enough positive political stories proves harder than expected! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra...
#2896 - TBT: Home Gym Affiliate Earns $80,000 05.12.2024 6:08
In this week’s “Throwback Thursday” segment, we hear from a side hustler whose passion for fitness transformed into a successful affiliate marketing blog. 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 no...
#2895 - Q&A: “Should I record my videos in portrait or landscape mode?” 04.12.2024 4:06
Today’s episode tackles a question about recording videos for multiple platforms. Should you shoot in portrait or landscape mode? And is there a way to record once and use the content everywhere? We’ve got answers and tips to streamline your video production. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their j...
#2894 - Q&A: “Can I do Substack, TikTok, podcast, and a paid membership?” 03.12.2024 4:49
In today’s episode, we help a creator who’s building a solo travel platform decide whether to focus on one content platform or expand to multiple channels like Substack, TikTok, and podcasts. 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&...
#2893 - First $1,000: Building a Business One Signature at a Time 02.12.2024 6:53
In this week’s First $1,000 segment, we hear from the owner of a California signature-gathering business, which collects signatures for ballot initiatives. He earns more than $1 on every signature—and this money adds up! 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 g...
#2892 - Q&A: “How will a new presidential administration impact side hustlers?” 01.12.2024 4:35
Today’s episode addresses what a new presidential administration could mean for small business owners and side hustlers. We’ll cover possible tax changes, regulatory shifts, and access to funding. 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...
#2891 - Q&A: “How to conduct competitor analysis for free?” 30.11.2024 5:19
In today’s episode, we dive into free and effective ways to analyze your competition. Learn to use simple Google searches, free tools, and social media insights to keep your side hustle ahead of the game. 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...
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