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PODCAST

Side Hustle School

Chris Guillebeau / Onward Project

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

business entrepreneurship

All Episodes

5:47

Ep. 2926 - Q&A: “Is it wise to offer a money-back...

Side Hustle School ·

2025/01/04

In today’s episode, we help a photographer decide whether to offer a money-back guarantee for his services. Learn how to build trust with clients while protecting your business from potential downsides. 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:

en

6:01

Ep. 2925 - Q&A: “How can I stand out in the coaching...

Side Hustle School ·

2025/01/03

In today’s episode, we help a leadership coach stand out in an oversaturated market. Learn how to identify your unique value, niche down, and attract your ideal clients with strategies that work. 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:

en

6:02

Ep. 2924 - TBT: Cookie ATM Becomes Pop-Up Hit

Side Hustle School ·

2025/01/02

In this week’s Throwback Thursday segment, we revisit two late-night bakers who created Oakland’s first cookie ATM. They share how this bold experiment evolved into a thriving pop-up and DIY cookie kit 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. Show notes: SideHustleSchool.com Email:

en

5:52

Ep. 2923 - Side Hustle School Season 9 Starts TODAY

Side Hustle School ·

2025/01/01

We’re back with an all-new season! Here’s how year nine (!) of Side Hustle School will work. Introducing new features, music, and another 365 days of episodes. 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:

en

5:05

#2922 - Q&A: “How can I start an ‘adopt don’t shop’...

Side Hustle School ·

2024/12/31

In today’s New Year’s Eve episode, we help a listener explore how to turn their passion for the ‘adopt, don’t shop’ movement 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.Show notes: SideHustleSchool.comEmail: team@sidehustleschool.comBe on the show:

en

6:12

#2921 - First $1,000: Office Furniture Blog Stands Up...

Side Hustle School ·

2024/12/30

In this week’s First $1,000 segment, we meet a web developer who turned his interest in ergonomic office furniture into a profitable side hustle. We explore how he built multiple niche websites that generated tens of thousands in commissions through Google AdSense.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

en

6:06

#2920 - Q&A: “Why did you give away your ‘Doing...

Side Hustle School ·

2024/12/29

In today’s episode, we dive into the strategy behind giving away an online course for free. Was this a crazy idea, a strategic plan, or something else?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.comEmail: team@sidehustleschool.comBe on the show:

en

4:36

#2919 - Q&A: “What are your predictions for next year?”

Side Hustle School ·

2024/12/28

In today’s episode, we dive into predictions for 2025—which is right around the corner! What trends, opportunities, and challenges should side hustlers and small business owners be preparing for?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.comEmail: team@sidehustleschool.comBe on

en

9:06

#2918 - Failure Friday: The Multi-Platform Freelance...

Side Hustle School ·

2024/12/27

In this week’s “Failure Friday” segment, we hear from a freelance graphic designer who found success on Upwork and decided to expand to Fiverr to grow her client base. However, the move to Fiverr led to a decline in client quality, causing issues with project expectations and delivery.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

en

8:02

#2917 - TBT: Analyst Turns Card Comparison Into Cash

Side Hustle School ·

2024/12/26

In this week’s “Throwback Thursday” segment, we hear from a fin-tech employee whose side project comparing credit cards grew into a profitable venture, earning $8,000/month in referral fees.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

en

6:31

#2916 - Q&A: “What are the top 3 things I should do...

Side Hustle School ·

2024/12/25

Merry Christmas! In today’s episode, we help a listener decide what to focus on next after gaining early traction with their 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 show: SideHustleSchool.com/questions Connect on

en

6:45

#2915 - Q&A: “Best tools for managing a shared...

Side Hustle School ·

2024/12/24

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

en

8:06

#2914 - First $1,000: Data Analyst Codes Fantasy...

Side Hustle School ·

2024/12/23

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

en

6:49

#2913 - Q&A: “How do I understand ROI when buying a...

Side Hustle School ·

2024/12/22

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

en

7:06

#2912 - Q&A: “I’ve been paying for subscriptions I...

Side Hustle School ·

2024/12/21

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

en

9:08

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

Side Hustle School ·

2024/12/20

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 who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A

en

8:11

#2910 - TBT: Graphic Artist Taps Into Planner Craze

Side Hustle School ·

2024/12/19

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

en

6:12

#2909 - Q&A: “How can I increase the average price...

Side Hustle School ·

2024/12/18

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:

en

7:45

#2908 - Q&A: “Should I hire micro-influencers to...

Side Hustle School ·

2024/12/17

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 the show:

en

8:11

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

Side Hustle School ·

2024/12/16

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.com Be on the show:

en

1,407 results

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