Side Hustle School

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Episodes

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Side Hustle School

Chris Guillebeau / Onward Project•sidehustleschool.com

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 https://lemonadamedia.com/

Episodes

#2909 - Q&A: “How can I increase the average price per order for my online store?”

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 includes free guided lessons and listener Q&A several days each week. Show notes: S...

Dec 18, 2024•4 min•Ep 2909•Transcript available on Metacast

#2908 - Q&A: “Should I hire micro-influencers to promote my brand?”

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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on ...

Dec 17, 2024•6 min•Ep 2908•Transcript available on Metacast

#2907 - First $1,000: Managing Airbnb Properties in Amsterdam

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&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.co...

Dec 16, 2024•6 min•Ep 2907•Transcript available on Metacast

#2906 - Q&A: “I need a sales script for cold emailing potential clients!”

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 and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehu...

Dec 15, 2024•5 min•Ep 2906•Transcript available on Metacast

#2905 - Q&A: ““What’s the best ticketing strategy for my event?”

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&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be...

Dec 14, 2024•5 min•Ep 2905•Transcript available on Metacast

#2904 - Failure Friday: Mobile Massage Service Gets Shut Down

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&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.c...

Dec 13, 2024•6 min•Ep 2904•Transcript available on Metacast

#2903 - TBT: Santa's Secretary Sees Seasonal Surge

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 show includes free guided lessons and listener Q&A several days each week. Show notes: SideH...

Dec 12, 2024•5 min•Ep 2903•Transcript available on Metacast

#2902 - Q&A: “How can I start a digital side hustle with no experience?”

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, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHus...

Dec 11, 2024•5 min•Ep 2902•Transcript available on Metacast

#2901 - Q&A: “Should you start a new hustle or scale what you already have?”

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 guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: t...

Dec 10, 2024•4 min•Ep 2901•Transcript available on Metacast

#2900 - First $1,000: Handyman Cashes In On Home Theater Boom

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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show...

Dec 09, 2024•7 min•Ep 2900•Transcript available on Metacast

#2899 - Q&A: “Can you profit on OnlyFans with non-adult content?”

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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.c...

Dec 08, 2024•6 min•Ep 2899•Transcript available on Metacast

#2898 - Q&A: “What are the hardest side hustles to start and operate?”

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 includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.co...

Dec 07, 2024•6 min•Ep 2898•Transcript available on Metacast

#2897 - Failure Friday: "Good Political News" Channel Runs Out of Stories

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 money without quitting their job. This year, the show includes free guided lessons and listener Q&am...

Dec 06, 2024•7 min•Ep 2897•Transcript available on Metacast

#2896 - TBT: Home Gym Affiliate Earns $80,000

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 notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/ques...

Dec 05, 2024•6 min•Ep 2896•Transcript available on Metacast

#2895 - Q&A: “Should I record my videos in portrait or landscape mode?”

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 job. This year, the show includes free guided lessons and listener Q&A several days each week. Sh...

Dec 04, 2024•4 min•Ep 2895•Transcript available on Metacast

#2894 - Q&A: “Can I do Substack, TikTok, podcast, and a paid membership?”

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&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be o...

Dec 03, 2024•5 min•Ep 2894•Transcript available on Metacast

#2893 - First $1,000: Building a Business One Signature at a Time

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 guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: t...

Dec 02, 2024•7 min•Ep 2893•Transcript available on Metacast

#2892 - Q&A: “How will a new presidential administration impact side hustlers?”

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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com...

Dec 01, 2024•5 min•Ep 2892•Transcript available on Metacast

#2891 - Q&A: “How to conduct competitor analysis for free?”

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 and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustlesc...

Nov 30, 2024•5 min•Ep 2891•Transcript available on Metacast

#2890 - Failure Friday: Sugar-Coated Advice Crumbles Cake Dreams

In this week’s Failure Friday segment, we hear from a passionate baker whose custom cake business quickly rises, only to fall flat due to misguided pricing strategies and well-meaning but bad advice from loved ones. 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@s...

Nov 29, 2024•7 min•Ep 2890•Transcript available on Metacast

#2889 - TBT: From House Flipper to Rental Property Guru

In this week’s “Throwback Thursday” segment, we revisit a side hustler whose real estate investing experience evolved into helping families purchase their first rental properties in distressed cities. 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...

Nov 28, 2024•7 min•Ep 2889•Transcript available on Metacast

#2888 - Q&A: “How to create a simple customer loyalty program for a small business?”

On today’s episode, we’re talking about how to create a simple, low-maintenance customer loyalty program for your side business. Did someone say punch card? 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 show: SideHustleSchool.com/qu...

Nov 27, 2024•5 min•Ep 2888•Transcript available on Metacast

#2887 - Q&A: “Is it easier or harder to start an online business today?”

In today’s episode, we explore whether it’s easier or harder to start an online business today compared to seven years ago. Find out how the landscape has changed and what it takes to stand out in a crowded market. 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@si...

Nov 26, 2024•5 min•Ep 2887•Transcript available on Metacast

#2886 - First $1,000: Licensing Digital Art to Cruise Lines

In this week’s “First $1K” segment, we hear from a digital artist who licensed their artwork to cruise lines for use on TVs and digital displays. Discover how this unique niche led to earning the artist her first $1,000. 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: t...

Nov 25, 2024•6 min•Ep 2886•Transcript available on Metacast

#2885 - Q&A: “How to increase the perceived value of digital products?”

In today’s episode, we discuss how to package and present digital products in a way that increases their perceived value. 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 show: SideHustleSchool.com/questions Connect on Instagram: @193c...

Nov 24, 2024•5 min•Ep 2885•Transcript available on Metacast

#2884 - Q&A: “Instagram Reels strategies for showcasing a product or service...”

On today’s episode, we’re breaking down how to use Instagram Reels to grow your side hustle. From product showcases to behind-the-scenes content, find out how you can create engaging Reels that capture attention and drive sales. 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 ...

Nov 23, 2024•5 min•Ep 2884•Transcript available on Metacast

#2883 - Failure Friday: Trademark Troubles Topple New Business

In this week’s Failure Friday segment, we follow a small business owner whose clever branding leads to an unexpected legal battle. 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 show: SideHustleSchool.com/questions Connect on Instagr...

Nov 22, 2024•6 min•Ep 2883•Transcript available on Metacast

#2882 - TBT: The Unlikely Algae Entrepreneur

In this week’s “Throwback Thursday” segment, we catch up with the owner of a small-scale algae farm in Wisconsin who’s ridden the wave of plant-based supplement popularity. 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 show: SideHus...

Nov 21, 2024•6 min•Ep 2882•Transcript available on Metacast

#2881 - Q&A: “How to ask for and gather customer testimonials?”

In this episode, we explore the best ways to gather customer testimonials for your side hustle. This is important! 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 show: SideHustleSchool.com/questions Connect on Instagram: @193countrie...

Nov 20, 2024•5 min•Ep 2881•Transcript available on Metacast

#2880 - Q&A: “How do you structure your day when balancing a 9-to-5 job?"

In this episode, we explore how to balance a full-time job with a side hustle. The struggle is real! 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 show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris'...

Nov 19, 2024•6 min•Ep 2880•Transcript available on Metacast