Side Hustle School

Dec 21 2024 2966 ep. 9 mins 19.3k
Side Hustle School Podcast artwork

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.

  Business
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#2912 - Q&A: “I’ve been paying for subscriptions I don’t use!”

Dec 21 2024 7 mins  
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 eac

#2911 - Failure Friday: When My Side Hustle Took Over My Life

Dec 20 2024 9 mins  
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

#2910 - TBT: Graphic Artist Taps Into Planner Craze

Dec 19 2024 8 mins  
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

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

Dec 18 2024 6 mins  
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.

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

Dec 17 2024 7 mins  
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 l

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

Dec 16 2024 8 mins  
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 l

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

Dec 15 2024 7 mins  
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

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

Dec 14 2024 6 mins  
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 a

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

Dec 13 2024 8 mins  
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

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

Dec 12 2024 6 mins  
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,