Chris Guillebeau

Side Hustle School

Business EN ↓ 3651 episodi

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.

Visita il sito del podcast e sostieni chi lo crea: sidehustleschool.com

Autore

Chris Guillebeau

Categoria

Business

Sito del podcast

sidehustleschool.com

Ultimo episodio

3 nov 2026

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Episodi

#2847 - TBT: Mixing Drinks and Making Money in Aspen 17.10.2024

In this week’s “Throwback Thursday” segment, we hear from a bartender who moved from Michigan to Aspen, Colorado, to take advantage of the lucrative opportunities in the high-end resort town.  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...

#2846 - Q&A: “"How can I transition from finance to my creative side hustle career?” 16.10.2024

In this episode, we'll explore practical strategies for a listener looking to transition a side hustle into a new full-time career, even while working a demanding 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 Q&A several days e...

#2845 - Q&A: “How to start a small marketing agency?” 15.10.2024

In this episode, we explore the steps to building a successful small marketing agency, including how to decide on an area of specialization. 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: SideHustl...

#2844 - First $1,000: Hospice Nurse Helps Families Prepare for Final Days 14.10.2024

In this week’s First $1,000 segment, we meet a former hospice nurse who launched a unique side hustle as a “death doula.” She shares how her compassionate approach to end-of-life care is changing how families navigate their final days with 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...

#2843 - Q&A: "How can I explain reiki more effectively to potential clients?" 13.10.2024

In this episode, we'll explore how alternative wellness practitioners can build awareness and educate potential clients about their services, so they can spend more time actually providing treatments. 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...

#2842 - Q&A: “How to start a reselling business with limited storage?” 12.10.2024

In this episode, we explore how to start a reselling business when you have limited storage space. Can you avoid the issue of inventory altogether?  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...

#2841 - Failure Friday: The Corporate Gig Where I Undersold Myself 11.10.2024

In this week’s “Failure Friday” segment, we hear from an industry expert who was invited to give a corporate talk at an oil company conference in Halifax. Just one problem: he didn’t know how much to charge, so he asked for much less than the company would have paid. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting...

#2840 - TBT: Austin Event Planner Goes Hard for SXSW 10.10.2024

In this week’s “Throwback Thursday” segment, we hear from an event planner in Austin who books many of the city’s tech parties and events, especially during the popular SXSW festival. 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...

#2839 - Q&A: "When is the right time to quit your job and go all-in?” 09.10.2024

In this episode, we'll explore the key milestones and financial targets that can signal when it's time to transition your side hustle into a full-time 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 listener Q&A several days each week. S...

#2838 - Q&A: “How can I diversify my side income streams?” 08.10.2024

In this episode, we discuss how to diversify your freelance income to create a more resilient business or 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: tea...

#2837 - First $1,000: NYC Exotic Petsetter Cares for Bearded Dragons 07.10.2024

In this week’s First $1,000 segment, we hear from a New York City exotic petsetter who sees everything from bearded dragons to chinchillas to axolotls—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. S...

#2836 - Q&A: “How to reduce newsletter churn?” 06.10.2024

In this episode, we tackle high churn rates in subscription-based newsletters. Learn how to keep subscribers engaged and active! 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...

#2835 - Q&A: “How to start a successful membership site?” 05.10.2024

In this episode, we explore how to create AND sustain a successful membership site. Learn about choosing the right platform, pricing strategies, and the best types of content to keep your members engaged. 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...

#2834 - Failure Friday: The Challenges of Helping Smokers Switch to Vaping 04.10.2024

In this week’s “Failure Friday” segment, we hear from a tech employee who tried to start a business helping smokers transition to vaping and other smokeless tobacco alternatives. Unfortunately, he struggled to attract paying clients. 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...

#2833 - TBT: Building a Cross-Atlantic Real Estate Business 03.10.2024

In this week’s “Throwback Thursday” segment, we hear from a British real estate agent who found success selling Bermuda condos to buyers in Florida.  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:...

#2832 - Q&A: “How to build an authentic personal brand?” 02.10.2024

In this episode, learn how to build a personal brand that’s authentic and impactful. Do you just post a bunch of selfies on Instagram, or is there more to 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, the show includes free guided lessons and listener Q&A several days each week. Sh...

#2831 - Q&A: “How to build and manage a remote team?” 01.10.2024

In this episode, we explore how to build and manage a remote team for your growing side hustle. How can you find the best candidates—and keep them around? 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...

#2830 - First $1,000: Passive Income with YouTube Toy Reviews 30.09.2024

In this week’s “First $1K” segment, we hear from a YouTuber who starts a toy review channel and gets paid for thousands of views. Might there be a channel waiting for YOU to launch next? 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...

#2829 - Q&A: “Best practices for automated follow-up emails?” 29.09.2024

In this episode, we explore how to set up effective automated follow-up email sequences—without being too annoying. 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...

#2828 - Q&A: “What’s the best way to organize a meetup?” 28.09.2024

In this episode, we discuss how to organize and promote a successful meetup or sales presentation on a budget—and how this can help your 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:...

#2827 - Failure Friday: Lessons from a Candle Subscription Box 27.09.2024

In this week’s “Failure Friday” segment, we hear from a candle seller who tries to start a subscription box business, but soon discovers a much better business in selling in bulk to restaurants. 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...

#2826 - TBT: Turning Small Items into Big Profits 26.09.2024

In this week’s “Throwback Thursday” segment, we hear from a woman who turned her passion for designing pins and stickers into a profitable business. Learn how she tackled the challenge of increasing her average order size and now earns $60,000 a year part-time. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their...

#2825 - Q&A: “When can I start getting paid for YouTube views?” 25.09.2024

In this episode, we discuss how to start earning money from YouTube views. Learn about the requirements for monetization, strategies to grow your channel quickly, and tips to maximize your 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 includes free guided lessons and list...

#2824 - Q&A: “How can I monetize my content on Threads?” 24.09.2024

In this episode, we explore how to monetize your presence on Meta’s Threads. More than 100 million users are on to something! 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 Ema...

#2823 - First $1,000: Artisan Chocolatier Hits Sweet Milestone 23.09.2024

In this week’s “First $1K” segment, we hear from an artisan chocolatier in Seattle who turns their passion for handcrafted chocolates into a profitable 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 listener Q&A several days each week....

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