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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

4:40

Ep. 2947 - Q&A: “What’s the best way to offer payment...

Side Hustle School ·

2025/01/25

In today’s episode, we help an online course creator set up payment plans that attract customers while minimizing risks. Learn the best strategies to balance accessibility and profitability. 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

en

5:39

Ep. 2946 - Q&A: “When should I hire a virtual...

Side Hustle School ·

2025/01/24

In today’s episode, we help a side hustler decide if it’s time to hire a virtual assistant. Learn how to assess your readiness, find the right help, and delegate tasks effectively without breaking the bank. 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

6:49

Ep. 2945 - TBT: Bringing STEM to Life with Custom...

Side Hustle School ·

2025/01/23

In this week’s Throwback Thursday segment, we hear how a San Jose educator scaled their DIY science kits. Learn how school partnerships and workshops helped them deliver hands-on STEM experiences to hundreds of kids every month. 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

7:05

Ep. 2944 - The $300,000 Bouncy Castle Drop-Shipping...

Side Hustle School ·

2025/01/22

A Texas man puts a bounce in his step by finding a uniquely profitable niche. This bouncy hustle earns multiple six-figures in its first year! 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

5:00

Ep. 2943 - Q&A: “Should I create a niche blog or a...

Side Hustle School ·

2025/01/21

In today’s episode, we help a new blogger decide whether to focus on a specific niche or go broad to grow faster. Learn why starting small and specific can give you the best chance for 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: SideHustleSchool.com Email: team@sidehustleschool.com

en

6:49

Ep. 2942 - First $1,000: Turning Central Park Picnics...

Side Hustle School ·

2025/01/20

In this week’s First $1,000 segment, we hear from an NYC event planner who started a pop-up picnic service in the city’s parks. Learn how she marketed her picnics and reached 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:

en

7:01

Ep. 2941 - Weekend Workshop: Sizing Up Your Ideas

Side Hustle School ·

2025/01/19

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: sizing up your ideas. 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

5:09

Ep. 2939 - Q&A: “How do I calculate the break-even...

Side Hustle School ·

2025/01/17

In today’s episode, we help a social media manager calculate her break-even point. Learn how to apply this essential business concept to a service-based business and use it to grow more strategically. 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

6:32

Ep. 2938 - TBT: Ghost Influencers and the Art of...

Side Hustle School ·

2025/01/16

In this week’s Throwback Thursday segment, we explore the rise of ghost influencers—anonymous personas creating real engagement for brands. Hear how one edgy social media manager turned this idea into a thriving 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

en

7:04

Ep. 2937 - Woman on Food Stamps Earns $86,000...

Side Hustle School ·

2025/01/15

In the face of adversity, a woman creates a series of online courses teaching the art of baking sourdough bread. Stop loafing around! If she can do it, you can too. 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

5:34

Ep. 2936 - Q&A: “What’s the downside of getting funded?”

Side Hustle School ·

2025/01/14

In today’s episode, we help a catering business owner weigh the risks of taking outside funding to grow her business. Learn about the potential downsides, from financial pressure to loss of control, and how to make the best decision. 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

5:44

Ep. 2935 - First $1,000: The High-Profit Second Life...

Side Hustle School ·

2025/01/13

In this week’s First $1,000 segment, we meet a repair enthusiast who’s giving gently used items a second life. He shares how he created a repair and resale business with unique product stories, quickly reaching his 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:

en

7:29

Ep. 2934 - Weekend Workshop: Beg, Borrow, or Steal Ideas

Side Hustle School ·

2025/01/12

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: the power of observation. 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

5:35

Ep. 2933 - Q&A: “How do I know if my idea is going to...

Side Hustle School ·

2025/01/11

In today’s episode, we help a listener validate their idea for a carpooling app for parents. Learn how to test demand, estimate costs, and spot red flags before investing too much time or 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

en

4:51

Ep. 2932 - Q&A: “Should I open a second location?”

Side Hustle School ·

2025/01/10

In today’s episode, we help a fitness studio owner decide if it’s the right time to open a second location. Learn how to evaluate your readiness, minimize risks, and expand without turning success into stress. 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

6:51

Ep. 2931 - TBT: From Gear Rentals to New Zealand...

Side Hustle School ·

2025/01/09

In this week’s Throwback Thursday segment, we revisit a side hustler who began renting camping gear to tourists in New Zealand. Now, they organize guided wilderness expeditions for beginner adventurers, helping clients from around the world experience the great outdoors. 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

en

6:18

Ep. 2930 - Role-Play ing Pastor Rolls The Dice On...

Side Hustle School ·

2025/01/08

This pastor had been side-hustling his entire adult life and was about to burn out. Luckily a familiar podcast showed him how to save time, sell products, and turn his role playing passion into profit. 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

5:14

Ep. 2929 - Q&A: “What can I learn from my website...

Side Hustle School ·

2025/01/07

In today’s episode, we help an online shop owner figure out what to focus on in her website analytics. Learn how to use conversion rates, bounce rates, and other key metrics to grow your e-commerce 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

6:16

Ep. 2928 - First $1,000: Micro-Courses for Fast Learning

Side Hustle School ·

2025/01/06

In this week’s First $1,000 segment, we hear from a Minneapolis teacher who turned her knowledge of children’s stories into a series of short, actionable online courses. Robin shares how she marketed her micro-courses and earned 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

en

9:48

2927 - Weekend Workshop: How to Spot a Profitable...

Side Hustle School ·

2025/01/05

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: learning to spot profitable ideas. 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

en

1,407 results

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