Chris Guillebeau

Side Hustle School

Business EN ↓ 3536 episodes

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.

Author

Chris Guillebeau

Episodes

#1539 - Failure Friday: Hand Sanitizer Makes Clean Getaway 19.03.2021 6:51

In this week’s “Failure Friday” segment, a hand sanitizer product line expansion encounters epic delays and misfortune for this natural body care products founder. 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 wee...

#1538 - TBT: Classy Throw Blankets Provide Deep Cover 18.03.2021 7:57

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Pacific Northwest resident who sells decorative knit throw blankets. 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. Share: #S...

BONUS: How to Manage Multiple Sources of Income 17.03.2021 6:09

Having more than one source of income is good—but it can also be confusing when it comes to tracking and tax reporting. This short bonus episode is brought to you by Quickbooks. 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...

#1537 - Q&A: Can I give people books in exchange for reviews? 17.03.2021 6:03

A listener is self-publishing on Kindle Direct Publishing and hopes to drum up reviews. Can she contact customers who’ve left reviews for other authors in the same genre? 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...

#1536 - Fan Scores Big with Marketplace for Football Shirts 16.03.2021 7:39

A football (soccer) shirt enthusiast turns his fashion passion into profits, overcoming a crippling field penalty given by Facebook. 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. Share: #SideHustleSchool Sh...

#1535 - Q&A: How can this listener attract new interest in “old skills?” 15.03.2021 5:47

A listener recently learned that morse code can do more than send SOS signals. Is there a resurgent interest in “old skills”? If so, how might she monetize 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. ...

#1534 - Software Engineer Publishes Technical Writing Guide 14.03.2021 9:12

After a computer programmer with a knack for technical writing is approached for a freelance gig, he ends up writing the book on the subject. 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. Share: #SideHustle...

#1533 - Q&A: What can we learn from Peloton? 13.03.2021 6:10

Today’s listener wants to know what we can learn from the winners, especially companies like Peloton and Mirror. What are the lessons for those of us who don’t have millions in venture capital? 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...

#1532 - Q&A: What's the deal with NFTs? 12.03.2021 6:22

A very timely question! Everyone is talking about non-fungible tokens (NFTs), digital art that is selling for millions of dollars. Is this a bubble? What do you need to know? In short: WTF is up with NFTs? 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...

#1531 - TBT: “Plant Influencer” Grows to Greatness 11.03.2021 7:37

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Toronto *plant influencer* who offers corporate workshops over Zoom. 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. Share: #S...

BONUS: How to Prepare for Life After COVID 10.03.2021 6:30

The end is near! Now that vaccination is well underway, we can safely envision a world without COVID-19. What does that look like? This short bonus episode is brought to you by Quickbooks. 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...

#1530 - Q&A: How about a directory of garage and yard sales? 10.03.2021 6:06

Today’s caller has an idea to create a directory of garage and yard sales. She thinks it’s a winner because so many people are trying to buy and resell items. What’s the best way to proceed? 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...

#1529 - Bikini Lover Finds Sea of Opportunity 09.03.2021 8:07

A Seattle-based product manager takes the plunge to design sustainable swimsuits. 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. Share: #SideHustleSchool Show notes: SideHustleSchool.com Twitter: @chrisguill...

#1528 - Q&A: Should I start a podcast OR YouTube channel? 08.03.2021 6:00

A listener is trying to decide between a podcast or YouTube channel. What are the pros and cons of each, and how can they 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. Share: #SideH...

#1527 - To Find Freelance Work, Look at Full-Time Job Listings 07.03.2021 8:01

A laid-off social media strategist gets creative, using LinkedIn job listings to find candidates for freelance work. One year later, he’s bringing in $10,000/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 we...

#1526 - Q&A: Get paid to help brands with their Terms & Conditions? 06.03.2021 5:53

Today’s caller wants to help brands improve their Terms & Conditions, also known as T&C. Can she design and license a template that companies will pay 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...

#1525 - Failure Friday: “A $300 mistake cost me $100,000” 05.03.2021 8:43

In this week’s new “Failure Friday” segment, we hear from the founder of a lifestyle and apparel brand who wakes up one day to find out he’s being sued. 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. Share:...

#1524 - TBT: “Hero’s Journal” Completes Epic Quest 04.03.2021 10:00

In this week’s “Throwback Thursday / Where are they now?” segment, we undertake a valiant quest to hear from the co-founder of a legendary journal. 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. Share: #Side...

#1523 - Q&A: Where should I direct my Pinterest traffic? 03.03.2021 5:10

A listener is interested in a new online marketplace that donates profits to charity. She’s getting attention from her Pinterest pins and wants to know where to direct traffic—to the new marketplace, or somewhere classic like Etsy? 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 incl...

#1522 - Student Makes Selling Sneakers Look Yeezy 02.03.2021 8:04

When a business student converses with a sneakerhead, they form an all-star pair to sell rare footwear. 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. Share: #SideHustleSchool Show notes: SideHustleSchool.co...

#1521 - Q&A: How can I create a cloud service consulting business? 01.03.2021 7:16

A listener is in charge of negotiating online services that his employer pays for. This skill is valuable, especially as more and more companies operate on a recurring payment model. How can he leverage this skill outside 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...

#1520 - Stay-At-Home Mom Starts Bamboo Baby Biz 28.02.2021 6:29

After taking time off in the later stages of a pregnancy, a new mom starts a business selling bamboo baby swaddles online. 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. Share: #SideHustleSchool Show notes:...

#1519 - Q&A: Should I create a pre-order campaign for my book launch? 27.02.2021 6:01

Today’s listener is self-publishing a book on personal finance—and he’s wondering about the launch process. Should he make the book available for pre-order or just put it up for sale? 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 s...

#1518 - Failure Friday: “We Accept Your Proposal… to Resign” 26.02.2021 7:34

In this week’s new “Failure Friday” segment, we hear from a young financial analyst who goes to his boss with a creative proposal to work remotely. He thinks it’s a great idea that will allow him to grow his side business, but the boss sees it quite differently. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting th...

#1517 - TBT: Pastry Chef Grows Retail Shop During Pandemic 25.02.2021 7:33

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a pastry chef who grows a retail shop in addition to her personalized wedding cake biz, all in the midst of the global pandemic. It’s an uphill batter… 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 inc...