Side Hustle School

By Chris Guillebeau / Onward Project

Business Careers

What's Side Hustle School about?

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.

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#1572 - Q&A: An idea for a...

04.21.2021

A listener has an idea to create a “Sober Happy Hour” taking place on Zoom. What’s the best way to structure it, and is this a moneymaking project? Side Hustle School features a new episode EVERY DAY, featuring detailed case ...

Side Hustle School episodes:

04.21.2021 #1572 - Q&A: An idea for a non-alcoholic Happy Hour A listener has an idea to create a “Sober Happy Hour” taking place on Zoom. What’s the best way to structure it, and is this a moneymaking project? Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
04.20.2021 #1571 - Civil Engineer Dismantles “90-Day Fiancé” Visa Problem After successfully navigating the difficult spousal visa process to bring his fiancé to the U.S., a civil engineer shows others how to do it. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ...
04.19.2021 #1570 - Q&A: Should I sell more headphones or expand to new categories? This listener has gone all-in with reselling headphones, and is making a good profit! Should she focus on one category and try to scale by selling more, or use what she’s learned to enter other categories? Side Hustle School features ...
04.18.2021 #1569 - Lifelong Superfan Gets Paid to Write Disney Blog A Disney superfan goes from journaling about the happiest place on Earth in a private notebook at age ten to sharing it with the whole world a decade later, earning $1,000/month from her passion project. Side Hustle School features a ...
04.17.2021 #1568 - Q&A: What are the main things to know when starting a podcast? A listener is taking the plunge and starting his own podcast! What are the top three things I wish I’d known when I began Side Hustle School? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
04.16.2021 #1567 - Failure Friday: “First Etsy crushed us, then Google pulled the plug…” In this week’s Failure Friday segment, we hear from a serial side hustle who makes a series of mistakes—but keeps going! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money ...
04.15.2021 #1566 - TBT: This Family Candle Business Is On Fire In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of an eco-friendly candle supplier. Profits are smoldering! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ...
04.14.2021 #1565 - Q&A: What are some good ways to repurpose content? Write it once, use it many times: this is the method known as “repurposing content.” Work smarter, not harder! Here’s how to do it. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ...
04.13.2021 #1564 - Customer Service Agent Becomes CBD Affiliate A long time software company rep spends ten years learning the affiliate marketing ropes, eventually cracking the code with a site providing reviews of CBD products. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
04.12.2021 #1563 - Q&A: How to automate an online dating profile consulting biz? This Australian listener wants to start a consulting biz to help improve dating profiles. How can she automate her booking process to avoid a lot of back-and-forth? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
04.11.2021 #1562 - RV Renter Revs Up Recurring Revenue A single mom turns her recreational vehicle into a money-making machine. 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 ...
04.10.2021 #1561 - Q&A: What’s the best way to share personal stories of recovery? A listener has struggled with an eating disorder and is now going through recovery. She wants to share her lessons and stories with others—what’s the best medium and process for this brave mission? Side Hustle School features a new episode ...
04.09.2021 #1560 - Failure Friday: Pandemic Shuts Down Himalayan Trekking Tours In this week’s Failure Friday segment, we hear from the founder of a Himalayan trekking co. who finds himself with zero business when Nepal shuts its borders. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
04.08.2021 #1559 - TBT: Budget Savvy Bridal Blog Gets Serious In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Budget Savvy Bride. She recently said “yes” to serious growth! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
04.07.2021 #1558 - Q&A: Can you sell a “home office in-a-box” kit? In today’s episode, we hear from a listener who has an idea to sell a home office in a box—a kit to help remote workers be happier and more productive. Side Hustle School features a new episode EVERY DAY, featuring ...
04.06.2021 #1557 - Catering Chef Cooks Up Private Meals When a catering chef learns to offer an in-home restaurant experience, he proves that knife guys don’t always finish last. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without ...
04.05.2021 #1556 - Q&A: How to start a paid club for people seeking multiple citizenships? Are you happy with your country of citizenship? Most people are, but not all —and some want to obtain multiple citizenships for tax or travel benefits. This listener wants to form a members-only club to bring these people together. Side ...
04.04.2021 #1555 - Healthcare Worker Publishes Children’s Book on Epidemiology As the global pandemic known as COVID-19 begins, a healthcare agency owner sets out to explain it to kids through the form of an entertaining story. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
04.03.2021 #1554 - Q&A: How can I publish my Army enlistment guide? An Army veteran wants to help new enlistees get a leg up in training. What’s the best format for his material? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money ...
04.02.2021 #1553 - Failure Friday: The Podcast Platform That Wasn’t In this week’s Failure Friday segment, we hear from John Lee Dumas, the founder of Entrepreneurs On Fire and author of a bestselling new book. Before he made millions of dollars with a podcasting community, he tried to start a ...
04.01.2021 #1552 - TBT: Multilingual Insurance Agent Creates Translation Course In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a multilingual insurance agent who creates an online course on the art of translation. Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
03.31.2021 #1551 - Q&A: Is podcast advertising more profitable than blog advertising? A listener is frustrated with the low earnings of blog ads. Does the podcast medium pay more? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. ...
03.30.2021 #1550 - Government Lawyer Lands Whale of a Side Gig A lawyer and long-time angler turns his passion for writing about the world of professional fishing into serious money. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting ...
03.29.2021 #1549 - Q&A: Is it too early to change my business name and brand? The owner of the Coddiwomple Craft Co. in Somerville, Massachusetts is thinking of changing its name—should she? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. ...
03.28.2021 #1548 - Origami-Loving Musician Doesn’t Mind Paperwork After canceling her concerts because of the pandemic, a working musician from New Zealand pays the bills with virtual origami lessons. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money ...
03.27.2021 #1547 - Q&A: How are people successful without social media? This listener hates the idea of using her Instagram or Facebook profile to share anything about her business. Do you have to use social to be successful? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ...
03.26.2021 #1546 - Failure Friday: NASA Sweatpants Not Ready for Liftoff In this week’s Failure Friday segment, we hear from the maker of Swoverall’s, a sweatpant-overall combo experiencing fantastic success—at least, until the brand tries to partner with NASA. Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
03.25.2021 #1545 - TBT: Pittsburgh Houseplant Merchant Blossoms During Pandemic In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a houseplant expert who opens a retail location right before the pandemic—a store that has adapted to challenges and is now in full bloom! Side Hustle ...
03.24.2021 BONUS: To the Moon! How to Buy Stock in Yourself You’ve heard about investing in a retirement account, but do you know how to invest in your own personal growth? This short bonus episode is brought to you by Quickbooks. Side Hustle School features a new episode EVERY DAY, featuring ...
03.24.2021 #1544 - Q&A: Does this hometown tourist guide have merit? The “Hoboken Girl” story of an online citywide news hub leads a listener to wonder if she can do something similar in her city. What are the prerequisites? Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
03.23.2021 #1543 - Children’s Librarian Builds Bra Business Frustrated by a lack of quality sports bras for muscular women, a children’s librarian and Crossfit athlete designs a solution. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without ...
03.22.2021 #1542 - Q&A: How can I develop an online memorial service? Dying is part of life for approximately 100% of us—and this listener has an idea to create an online memorial service for people who are unable to attend a loved one’s funeral. Side Hustle School features a new episode EVERY ...
03.21.2021 #1541 - Two Friends Create Questionable Card Game When a writer and a game designer want to learn more about their friends' personal lives, they play for keeps and develop a game that puts all the cards on the table. Side Hustle School features a new episode EVERY ...
03.20.2021 #1540 - Q&A: Would you join an introvert's networking club? With introverts getting a lot of attention these days, might it be worth it to create some type of networking club for them—or is this exactly the thing they don’t want? Side Hustle School features a new episode EVERY DAY, ...
03.19.2021 #1539 - Failure Friday: Hand Sanitizer Makes Clean Getaway 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 ...
03.18.2021 #1538 - TBT: Classy Throw Blankets Provide Deep Cover 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 ...
03.17.2021 BONUS: How to Manage Multiple Sources of Income 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 ...
03.17.2021 #1537 - Q&A: Can I give people books in exchange for reviews? 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 ...
03.16.2021 #1536 - Fan Scores Big with Marketplace for Football Shirts 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 ...
03.15.2021 #1535 - Q&A: How can this listener attract new interest in “old skills?” 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 ...
03.14.2021 #1534 - Software Engineer Publishes Technical Writing Guide 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 ...
03.13.2021 #1533 - Q&A: What can we learn from Peloton? 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 ...
03.12.2021 #1532 - Q&A: What's the deal with NFTs? 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 ...
03.11.2021 #1531 - TBT: “Plant Influencer” Grows to Greatness 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 ...
03.10.2021 BONUS: How to Prepare for Life After COVID 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 ...
03.10.2021 #1530 - Q&A: How about a directory of garage and yard sales? 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 ...
03.09.2021 #1529 - Bikini Lover Finds Sea of Opportunity 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 ...
03.08.2021 #1528 - Q&A: Should I start a podcast OR YouTube channel? 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 ...
03.07.2021 #1527 - To Find Freelance Work, Look at Full-Time Job Listings 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 ...
03.06.2021 #1526 - Q&A: Get paid to help brands with their Terms & Conditions? 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 ...

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